ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

B(C6F5)3-Catalyzed Hydrosilation of Imines via Silyliminium Intermediates

View Author Information
Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 Canada
Cite this: Org. Lett. 2000, 2, 24, 3921–3923
Publication Date (Web):November 10, 2000
https://doi.org/10.1021/ol006695q
Copyright © 2000 American Chemical Society

    Article Views

    4920

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Read OnlinePDF (46 KB)
    Supporting Info (1)»

    Abstract

    Abstract Image

    A broad range of benzaldimines and ketimines can be hydrosilated efficiently, employing B(C6F5)3 as a catalyst in conjunction with PhMe2SiH. Spectral evidence supports the intermediacy of a silyliminium cation with a hydridoborate counterion formed via abstraction of a hydride from PhMe2SiH by B(C6F5)3 in the presence of imines.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    Supporting Information Available

    ARTICLE SECTIONS
    Jump To

    Experimental details, including complete spectral data for 1. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 325 publications.

    1. Jan-Willem Lamberink-Ilupeju, Mathew J. Willans, Joe B. Gilroy, James J. Noël, Johanna M. Blacquiere, Paul J. Ragogna. Multicomponent Synthesis of Poly(α-aminophosphine chalcogenide)s and Subsequent Depolymerization. Inorganic Chemistry 2023, 62 (37) , 15104-15109. https://doi.org/10.1021/acs.inorgchem.3c02039
    2. Leah K. Oliemuller, Curtis E. Moore, Christine M. Thomas. Electronic and Structural Variations of a Nickel(0) N-Heterocyclic Phosphenium Complex in Comparison to Group 10 Analogues. Inorganic Chemistry 2022, 61 (48) , 19440-19451. https://doi.org/10.1021/acs.inorgchem.2c03302
    3. Joshua Clarke, Youngran Seo, Michel R. Gagné, Trandon A. Bender. Achieving Site-Selective C–O Bond Reduction for High-Value Cellulosic Valorization. ACS Catalysis 2022, 12 (22) , 14220-14226. https://doi.org/10.1021/acscatal.2c04768
    4. Kuldeep Singh, Idan Avigdori, Alexander Kaushansky, Natalia Fridman, Dor Toledano, Mark Gandelman. New Generation of Nitrenium Salts: Catalytic Hydrosilylation of Imines and a Mechanism of Action of Nitrogen Lewis Acids. ACS Catalysis 2022, 12 (12) , 6831-6839. https://doi.org/10.1021/acscatal.2c01297
    5. Deepak Ranolia, Idan Avigdori, Kuldeep Singh, Aleksandr Koronatov, Natalia Fridman, Mark Gandelman. Triazolium Salts as Lewis Acid Catalysts. Organic Letters 2022, 24 (22) , 3915-3919. https://doi.org/10.1021/acs.orglett.2c01108
    6. Cassandre C. Bories, Marion Barbazanges, Etienne Derat, Marc Petit. Implication of a Silyl Cobalt Dihydride Complex as a Useful Catalyst for the Hydrosilylation of Imines. ACS Catalysis 2021, 11 (22) , 14262-14273. https://doi.org/10.1021/acscatal.1c03886
    7. Huiling Wen, Nianhua Luo, Qianheng Zhu, Renshi Luo. Amide Iridium Complexes As Catalysts for Transfer Hydrogenation Reduction of N-sulfonylimine. The Journal of Organic Chemistry 2021, 86 (5) , 3850-3859. https://doi.org/10.1021/acs.joc.0c02680
    8. Kuldeep Jaiswal, Karina Chulsky, Mark Gandelman, Roman Dobrovetsky. O-Carboranylene versus Phenylene Backbones in Cyclization Reactions of 1,2 Diketones with Hydrosilanes. Organometallics 2020, 39 (23) , 4232-4237. https://doi.org/10.1021/acs.organomet.0c00208
    9. Iruthayaraj Avinash, Sabeeha Parveen, Ganapathi Anantharaman. Backbone Boron-Functionalized Imidazoles/Imidazolium Salts: Synthesis, Structure, Metalation Studies, and Fluoride Sensing Properties. Inorganic Chemistry 2020, 59 (8) , 5646-5661. https://doi.org/10.1021/acs.inorgchem.0c00348
    10. Travis Lundrigan, Erin N. Welsh, Toren Hynes, Chieh-Hung Tien, Matt R. Adams, Kayelani R. Roy, Katherine N. Robertson, Alexander W. H. Speed. Enantioselective Imine Reduction Catalyzed by Phosphenium Ions. Journal of the American Chemical Society 2019, 141 (36) , 14083-14088. https://doi.org/10.1021/jacs.9b07293
    11. Hui Peng, Jinhui Ma, Lingfei Duan, Guangwen Zhang, Biaolin Yin. CuH-Catalyzed Synthesis of 3-Hydroxyindolines and 2-Aryl-3H-indol-3-ones from o-Alkynylnitroarenes, Using Nitro as Both the Nitrogen and Oxygen Source. Organic Letters 2019, 21 (16) , 6194-6198. https://doi.org/10.1021/acs.orglett.9b01849
    12. Benedicta Assoah, Luis F. Veiros, Nuno R. Candeias. Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines. Organic Letters 2019, 21 (5) , 1402-1406. https://doi.org/10.1021/acs.orglett.9b00121
    13. Hongcai Chen, Lina Yan, Haiyan Wei. Mechanism of Boron-Catalyzed N-Alkylation of Primary and Secondary Arylamines with Ketones Using Silanes under “Wet” Conditions. Organometallics 2018, 37 (21) , 3698-3707. https://doi.org/10.1021/acs.organomet.8b00405
    14. Jianbo Zhang, Sehoon Park, Sukbok Chang. Catalytic Access to Bridged Sila-N-heterocycles from Piperidines via Cascade sp3 and sp2 C–Si Bond Formation. Journal of the American Chemical Society 2018, 140 (41) , 13209-13213. https://doi.org/10.1021/jacs.8b08733
    15. Subhrashis Banerjee, Kumar Vanka. B(C6F5)3: Catalyst or Initiator? Insights from Computational Studies into Surrogate Silicon Chemistry. ACS Catalysis 2018, 8 (7) , 6163-6176. https://doi.org/10.1021/acscatal.7b04489
    16. Rui Wang, Mengyue Ma, Xu Gong, Grace B. Panetti, Xinyuan Fan, Patrick J. Walsh. Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water. Organic Letters 2018, 20 (8) , 2433-2436. https://doi.org/10.1021/acs.orglett.8b00778
    17. Lipeng Wu, Saurabh S. Chitnis, Haijun Jiao, Vincent T. Annibale, and Ian Manners . Non-Metal-Catalyzed Heterodehydrocoupling of Phosphines and Hydrosilanes: Mechanistic Studies of B(C6F5)3-Mediated Formation of P–Si Bonds. Journal of the American Chemical Society 2017, 139 (46) , 16780-16790. https://doi.org/10.1021/jacs.7b09175
    18. Qin Yin, Yashar Soltani, Rebecca L. Melen, and Martin Oestreich . BArF3-Catalyzed Imine Hydroboration with Pinacolborane Not Requiring the Assistance of an Additional Lewis Base. Organometallics 2017, 36 (13) , 2381-2384. https://doi.org/10.1021/acs.organomet.7b00381
    19. Shibdas Banerjee, Yun-Fang Yang, Ian D. Jenkins, Yong Liang, Anton A. Toutov, Wen-Bo Liu, David P. Schuman, Robert H. Grubbs, Brian M. Stoltz, Elizabeth H. Krenske, Kendall N. Houk, and Richard N. Zare . Ionic and Neutral Mechanisms for C–H Bond Silylation of Aromatic Heterocycles Catalyzed by Potassium tert-Butoxide. Journal of the American Chemical Society 2017, 139 (20) , 6880-6887. https://doi.org/10.1021/jacs.6b13032
    20. Mathew D. Anker, Merle Arrowsmith, Rory L. Arrowsmith, Michael S. Hill, and Mary F. Mahon . Alkaline-Earth Derivatives of the Reactive [HB(C6F5)3]− Anion. Inorganic Chemistry 2017, 56 (10) , 5976-5983. https://doi.org/10.1021/acs.inorgchem.7b00678
    21. Jorge Escorihuela and Han Zuilhof . Rapid Surface Functionalization of Hydrogen-Terminated Silicon by Alkyl Silanols. Journal of the American Chemical Society 2017, 139 (16) , 5870-5876. https://doi.org/10.1021/jacs.7b01106
    22. Carl-Hugo Pélisson, Takahiro Nakanishi, Yang Zhu, Kei Morisato, Toshiyuki Kamei, Ayaka Maeno, Hironori Kaji, Shunki Muroyama, Masamoto Tafu, Kazuyoshi Kanamori, Toyoshi Shimada, and Kazuki Nakanishi . Grafted Polymethylhydrosiloxane on Hierarchically Porous Silica Monoliths: A New Path to Monolith-Supported Palladium Nanoparticles for Continuous Flow Catalysis Applications. ACS Applied Materials & Interfaces 2017, 9 (1) , 406-412. https://doi.org/10.1021/acsami.6b12653
    23. Youngchan Kim, Ramesh B. Dateer, and Sukbok Chang . Borane-Catalyzed Selective Hydrosilylation of Internal Ynamides Leading to β-Silyl (Z)-Enamides. Organic Letters 2017, 19 (1) , 190-193. https://doi.org/10.1021/acs.orglett.6b03485
    24. Kayla Jakobsson, Terry Chu, and Georgii I. Nikonov . Hydrosilylation of Olefins Catalyzed by Well-Defined Cationic Aluminum Complexes: Lewis Acid versus Insertion Mechanisms. ACS Catalysis 2016, 6 (11) , 7350-7356. https://doi.org/10.1021/acscatal.6b01694
    25. Qiwen Zhou, Lanqiong Zhang, Wei Meng, Xiangqing Feng, Jing Yang, and Haifeng Du . Borane-Catalyzed Transfer Hydrogenations of Pyridines with Ammonia Borane. Organic Letters 2016, 18 (20) , 5189-5191. https://doi.org/10.1021/acs.orglett.6b02610
    26. Trandon A. Bender, Jennifer A. Dabrowski, Hongyu Zhong, and Michel R. Gagné . Diastereoselective B(C6F5)3-Catalyzed Reductive Carbocyclization of Unsaturated Carbohydrates. Organic Letters 2016, 18 (16) , 4120-4123. https://doi.org/10.1021/acs.orglett.6b02050
    27. Qi Zhang, Hai-Zhu Yu, and Yao Fu . Theoretical Study of Ir-Catalyzed Chemoselective C1–O Reduction of Glucose with Silane. Organometallics 2016, 35 (15) , 2473-2479. https://doi.org/10.1021/acs.organomet.6b00347
    28. Hidekazu Arii, Yuto Yano, Kenichi Nakabayashi, Syuhei Yamaguchi, Masaki Yamamura, Kunio Mochida, and Takayuki Kawashima . Regioselective and Stereospecific Dehydrogenative Annulation Utilizing Silylium Ion-Activated Alkenes. The Journal of Organic Chemistry 2016, 81 (15) , 6314-6319. https://doi.org/10.1021/acs.joc.6b00793
    29. N. von Wolff, G. Lefèvre, J.-C. Berthet, P. Thuéry, and T. Cantat . Implications of CO2 Activation by Frustrated Lewis Pairs in the Catalytic Hydroboration of CO2: A View Using N/Si+ Frustrated Lewis Pairs. ACS Catalysis 2016, 6 (7) , 4526-4535. https://doi.org/10.1021/acscatal.6b00421
    30. Xiaoshuang Ning, Jiandi Wang, and Haiyan Wei . New Insights into Mechanism of Molybdenum(VI)–Dioxo Complex Catalyzed Hydrosilylation of Carbonyls: An Alternative Model for Activating Si–H Bond. The Journal of Physical Chemistry A 2016, 120 (24) , 4167-4178. https://doi.org/10.1021/acs.jpca.6b01978
    31. Lars Süsse, Julia Hermeke, and Martin Oestreich . The Asymmetric Piers Hydrosilylation. Journal of the American Chemical Society 2016, 138 (22) , 6940-6943. https://doi.org/10.1021/jacs.6b03443
    32. Pei-Qiang Huang, Qi-Wei Lang, and Yan-Rong Wang . Mild Metal-Free Hydrosilylation of Secondary Amides to Amines. The Journal of Organic Chemistry 2016, 81 (10) , 4235-4243. https://doi.org/10.1021/acs.joc.6b00572
    33. Meera Mehta, Isaac Garcia de la Arada, Manuel Perez, Digvijay Porwal, Martin Oestreich, and Douglas W. Stephan . Metal-Free Phosphine Oxide Reductions Catalyzed by B(C6F5)3 and Electrophilic Fluorophosphonium Cations. Organometallics 2016, 35 (7) , 1030-1035. https://doi.org/10.1021/acs.organomet.6b00158
    34. Valerio Fasano, James E. Radcliffe, and Michael J. Ingleson . B(C6F5)3-Catalyzed Reductive Amination using Hydrosilanes. ACS Catalysis 2016, 6 (3) , 1793-1798. https://doi.org/10.1021/acscatal.5b02896
    35. Xiaoyu Ren and Haifeng Du . Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds. Journal of the American Chemical Society 2016, 138 (3) , 810-813. https://doi.org/10.1021/jacs.5b13104
    36. Narasimhulu Gandhamsetty, Sehoon Park, and Sukbok Chang . Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp3 C–Si Bonds. Journal of the American Chemical Society 2015, 137 (48) , 15176-15184. https://doi.org/10.1021/jacs.5b09209
    37. Narasimhulu Gandhamsetty, Jinseong Jeong, Juhyeon Park, Sehoon Park, and Sukbok Chang . Boron-Catalyzed Silylative Reduction of Nitriles in Accessing Primary Amines and Imines. The Journal of Organic Chemistry 2015, 80 (14) , 7281-7287. https://doi.org/10.1021/acs.joc.5b00941
    38. Kodai Saito, Kazumi Kondo, and Takahiko Akiyama . B(C6F5)3-Catalyzed Hydrodesulfurization Using Hydrosilanes – Metal-Free Reduction of Sulfides. Organic Letters 2015, 17 (13) , 3366-3369. https://doi.org/10.1021/acs.orglett.5b01651
    39. Xiaoting Fan, Junhao Zheng, Zhen Hua Li, and Huadong Wang . Organoborane Catalyzed Regioselective 1,4-Hydroboration of Pyridines. Journal of the American Chemical Society 2015, 137 (15) , 4916-4919. https://doi.org/10.1021/jacs.5b03147
    40. Sebastian Keess, Antoine Simonneau, and Martin Oestreich . Direct and Transfer Hydrosilylation Reactions Catalyzed by Fully or Partially Fluorinated Triarylboranes: A Systematic Study. Organometallics 2015, 34 (4) , 790-799. https://doi.org/10.1021/om501284a
    41. Jiandi Wang, Liangfang Huang, Xiaodi Yang, and Haiyan Wei . Mechanistic Investigation Into Catalytic Hydrosilylation with a High-Valent Ruthenium(VI)–Nitrido Complex: A DFT Study. Organometallics 2015, 34 (1) , 212-220. https://doi.org/10.1021/om501071n
    42. Ken Sakata and Hiroshi Fujimoto . Quantum Chemical Study of the Reaction of 3-(Trimethylsilyl)cyclohexa-1,4-dienes with B(C6F5)3. Organometallics 2015, 34 (1) , 236-241. https://doi.org/10.1021/om501095e
    43. Narasimhulu Gandhamsetty, Seewon Joung, Sung-Woo Park, Sehoon Park, and Sukbok Chang . Boron-Catalyzed Silylative Reduction of Quinolines: Selective sp3 C–Si Bond Formation. Journal of the American Chemical Society 2014, 136 (48) , 16780-16783. https://doi.org/10.1021/ja510674u
    44. Nirmalya Moitra, Shun Ichii, Toshiyuki Kamei, Kazuyoshi Kanamori, Yang Zhu, Kazuyuki Takeda, Kazuki Nakanishi, and Toyoshi Shimada . Surface Functionalization of Silica by Si–H Activation of Hydrosilanes. Journal of the American Chemical Society 2014, 136 (33) , 11570-11573. https://doi.org/10.1021/ja504115d
    45. Ryan C. Chadwick, Vladimir Kardelis, Philip Lim, and Alex Adronov . Metal-Free Reduction of Secondary and Tertiary N-Phenyl Amides by Tris(pentafluorophenyl)boron-Catalyzed Hydrosilylation. The Journal of Organic Chemistry 2014, 79 (16) , 7728-7733. https://doi.org/10.1021/jo501299j
    46. Jens Mohr, Mustafa Durmaz, Elisabeth Irran, and Martin Oestreich . Tris(5,6,7,8-tetrafluoronaphthalen-2-yl)borane, a Partially Fluorinated Boron Lewis Acid with Fluorination Distal to the Boron Atom. Organometallics 2014, 33 (5) , 1108-1111. https://doi.org/10.1021/om500128a
    47. Wenmin Wang, Piao Gu, Yiou Wang, and Haiyan Wei . Theoretical Study of POCOP-Pincer Iridium(III)/Iron(II) Hydride Catalyzed Hydrosilylation of Carbonyl Compounds: Hydride Not Involved in the Iridium(III) System but Involved in the Iron(II) System. Organometallics 2014, 33 (4) , 847-857. https://doi.org/10.1021/om400634w
    48. Max M. Hansmann, Rebecca L. Melen, Frank Rominger, A. Stephen K. Hashmi, and Douglas W. Stephan . Activation of Alkynes with B(C6F5)3 – Boron Allylation Reagents Derived from Propargyl Esters. Journal of the American Chemical Society 2014, 136 (2) , 777-782. https://doi.org/10.1021/ja4110842
    49. Ken Sakata and Hiroshi Fujimoto . Quantum Chemical Study of B(C6F5)3-Catalyzed Hydrosilylation of Carbonyl Group. The Journal of Organic Chemistry 2013, 78 (24) , 12505-12512. https://doi.org/10.1021/jo402195x
    50. Yanfeng Jiang, Wenjing Huang, Helmut W. Schmalle, Olivier Blacque, Thomas Fox, and Heinz Berke . Efficient Lewis Acid Promoted Alkene Hydrogenations Using Dinitrosyl Rhenium(−I) Hydride Catalysts. Organometallics 2013, 32 (23) , 7043-7052. https://doi.org/10.1021/om400733u
    51. Kristine Müther, Jens Mohr, and Martin Oestreich . Silylium Ion Promoted Reduction of Imines with Hydrosilanes. Organometallics 2013, 32 (22) , 6643-6646. https://doi.org/10.1021/om4002796
    52. Holger Braunschweig, Alexander Damme, Christian Hörl, Thomas Kupfer, and Johannes Wahler . Si–H Bond Activation at the Boron Center of Pentaphenylborole. Organometallics 2013, 32 (22) , 6800-6803. https://doi.org/10.1021/om4005934
    53. Julia Hermeke, Marius Mewald, and Martin Oestreich . Experimental Analysis of the Catalytic Cycle of the Borane-Promoted Imine Reduction with Hydrosilanes: Spectroscopic Detection of Unexpected Intermediates and a Refined Mechanism. Journal of the American Chemical Society 2013, 135 (46) , 17537-17546. https://doi.org/10.1021/ja409344w
    54. Jordan W. Thomson, Jillian A. Hatnean, Jeff J. Hastie, Andrew Pasternak, Douglas W. Stephan, and Preston A. Chase . Improving the Industrial Feasibility of Metal-Free Hydrogenation Catalysts Using Chemical Scavengers. Organic Process Research & Development 2013, 17 (10) , 1287-1292. https://doi.org/10.1021/op4000847
    55. Tomáš Strašák, Jan Sýkora, Martin Lamač, Jiří Kubišta, Michal Horáček, Róbert Gyepes, and Jiří Pinkas . Reactivity of a Titanocene Pendant Si–H Group toward Alcohols. Unexpected Formation of Siloxanes from the Reaction of Hydrosilanes and Ph3COH Catalyzed by B(C6F5)3. Organometallics 2013, 32 (15) , 4122-4129. https://doi.org/10.1021/om400253g
    56. Takuya Yokosaka, Hiroki Nakayama, Tetsuhiro Nemoto, and Yasumasa Hamada . Acid-promoted Cascade Cyclization to Produce Fused-polycyclic Indole Derivatives. Organic Letters 2013, 15 (12) , 2978-2981. https://doi.org/10.1021/ol401128h
    57. Peter T. K. Lee, Miranda K. Skjel, and Lisa Rosenberg . Borane-Catalyzed Si–H Activation Routes to Polysilanes Containing Thiolato Side Chains. Organometallics 2013, 32 (6) , 1575-1578. https://doi.org/10.1021/om301246z
    58. Yanfeng Jiang, Birgitta Schirmer, Olivier Blacque, Thomas Fox, Stefan Grimme, and Heinz Berke . The “Catalytic Nitrosyl Effect”: NO Bending Boosting the Efficiency of Rhenium Based Alkene Hydrogenations. Journal of the American Chemical Society 2013, 135 (10) , 4088-4102. https://doi.org/10.1021/ja400135d
    59. Adrian Y. Houghton, Virve A. Karttunen, Cheng Fan, Warren E. Piers, and Heikki M. Tuononen . Mechanistic Studies on the Metal-Free Activation of Dihydrogen by Antiaromatic Pentarylboroles. Journal of the American Chemical Society 2013, 135 (2) , 941-947. https://doi.org/10.1021/ja311842r
    60. Jinhwa Heo, Taegon Kang, Se Gyu Jang, Dong Soo Hwang, Jason M. Spruell, Kato L. Killops, J. Herbert Waite, and Craig J. Hawker . Improved Performance of Protected Catecholic Polysiloxanes for Bioinspired Wet Adhesion to Surface Oxides. Journal of the American Chemical Society 2012, 134 (49) , 20139-20145. https://doi.org/10.1021/ja309044z
    61. Andreas Berkefeld, Warren E. Piers, Masood Parvez, Ludovic Castro, Laurent Maron, and Odile Eisenstein . Carbon Monoxide Activation via O-Bound CO Using Decamethylscandocinium–Hydridoborate Ion Pairs. Journal of the American Chemical Society 2012, 134 (26) , 10843-10851. https://doi.org/10.1021/ja300591v
    62. Andrey Y. Khalimon, Warren E. Piers, James M. Blackwell, David J. Michalak, and Masood Parvez . A Photo Lewis Acid Generator (PhLAG): Controlled Photorelease of B(C6F5)3. Journal of the American Chemical Society 2012, 134 (23) , 9601-9604. https://doi.org/10.1021/ja3042977
    63. Brett A. Kamino, Bridget Mills, Christopher Reali, Michael J. Gretton, Michael A. Brook, and Timothy P. Bender . Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials. The Journal of Organic Chemistry 2012, 77 (4) , 1663-1674. https://doi.org/10.1021/jo2020906
    64. Felix Schulz, Victor Sumerin, Sami Heikkinen, Björn Pedersen, Cong Wang, Michiko Atsumi, Markku Leskelä, Timo Repo, Pekka Pyykkö, Winfried Petry, and Bernhard Rieger . Molecular Hydrogen Tweezers: Structure and Mechanisms by Neutron Diffraction, NMR, and Deuterium Labeling Studies in Solid and Solution. Journal of the American Chemical Society 2011, 133 (50) , 20245-20257. https://doi.org/10.1021/ja206394w
    65. Warren E. Piers, Adam J. V. Marwitz, and Lauren G. Mercier . Mechanistic Aspects of Bond Activation with Perfluoroarylboranes. Inorganic Chemistry 2011, 50 (24) , 12252-12262. https://doi.org/10.1021/ic2006474
    66. David D. Schnaars, Guang Wu, and Trevor W. Hayton . Silylation of the Uranyl Ion Using B(C6F5)3-Activated Et3SiH. Inorganic Chemistry 2011, 50 (19) , 9642-9649. https://doi.org/10.1021/ic201385h
    67. Andrew E. Ashley, Thomas J. Herrington, Gregory G. Wildgoose, Hasna Zaher, Amber L. Thompson, Nicholas H. Rees, Tobias Krämer, and Dermot O’Hare . Separating Electrophilicity and Lewis Acidity: The Synthesis, Characterization, and Electrochemistry of the Electron Deficient Tris(aryl)boranes B(C6F5)3–n(C6Cl5)n (n = 1–3). Journal of the American Chemical Society 2011, 133 (37) , 14727-14740. https://doi.org/10.1021/ja205037t
    68. Adam J. V. Marwitz, Jason L. Dutton, Lauren G. Mercier, and Warren E. Piers . Dihydrogen Activation with tBu3P/B(C6F5)3: A Chemically Competent Indirect Mechanism via in Situ-Generated p-tBu2P–C6F4–B(C6F5)2. Journal of the American Chemical Society 2011, 133 (26) , 10026-10029. https://doi.org/10.1021/ja203214f
    69. David D. Schnaars, Guang Wu, and Trevor W. Hayton . Borane-Mediated Silylation of a Metal–Oxo Ligand. Inorganic Chemistry 2011, 50 (11) , 4695-4697. https://doi.org/10.1021/ic2008649
    70. Gary A. Molander, Nicolas Fleury-Brégeot, and Marie-Aude Hiebel . Synthesis and Cross-Coupling of Sulfonamidomethyltrifluoroborates. Organic Letters 2011, 13 (7) , 1694-1697. https://doi.org/10.1021/ol200202g
    71. Brett A. Kamino, John B. Grande, Michael A. Brook, and Timothy P. Bender . Siloxane−Triarylamine Hybrids: Discrete Room Temperature Liquid Triarylamines via the Piers−Rubinsztajn Reaction. Organic Letters 2011, 13 (1) , 154-157. https://doi.org/10.1021/ol102607v
    72. Meghan A. Dureen, Christopher C. Brown, and Douglas W. Stephan. Deprotonation and Addition Reactions of Frustrated Lewis Pairs with Alkynes. Organometallics 2010, 29 (23) , 6594-6607. https://doi.org/10.1021/om1009044
    73. Cheng Fan, Lauren G. Mercier, Warren E. Piers, Heikki M. Tuononen and Masood Parvez . Dihydrogen Activation by Antiaromatic Pentaarylboroles. Journal of the American Chemical Society 2010, 132 (28) , 9604-9606. https://doi.org/10.1021/ja105075h
    74. Roy M. Malamakal, Whitney R. Hess and Todd A. Davis. Highly Efficient Diastereoselective Reduction of α-Fluoroimines. Organic Letters 2010, 12 (10) , 2186-2189. https://doi.org/10.1021/ol100647b
    75. Christopher J. Lata and Cathleen M. Crudden . Dramatic Effect of Lewis Acids on the Rhodium-Catalyzed Hydroboration of Olefins. Journal of the American Chemical Society 2010, 132 (1) , 131-137. https://doi.org/10.1021/ja904142m
    76. KaKing Yan, Brianna M. Upton, Arkady Ellern and Aaron D. Sadow. Lewis Acid-Mediated β-Hydride Abstraction Reactions of Divalent M(C(SiHMe2)3)2THF2 (M = Ca, Yb). Journal of the American Chemical Society 2009, 131 (42) , 15110-15111. https://doi.org/10.1021/ja9070865
    77. Meghan A. Dureen, Gregory C. Welch, Thomas M. Gilbert and Douglas W. Stephan . Heterolytic Cleavage of Disulfides by Frustrated Lewis Pairs. Inorganic Chemistry 2009, 48 (20) , 9910-9917. https://doi.org/10.1021/ic901590s
    78. On-Yi Lee, Ka-Lun Law and Dan Yang. Secondary Amine Formation from Reductive Amination of Carbonyl Compounds Promoted by Lewis Acid Using the InCl3/Et3SiH System. Organic Letters 2009, 11 (15) , 3302-3305. https://doi.org/10.1021/ol901111g
    79. Tibor András Rokob, Andrea Hamza, András Stirling and Imre Pápai. On the Mechanism of B(C6F5)3-Catalyzed Direct Hydrogenation of Imines: Inherent and Thermally Induced Frustration. Journal of the American Chemical Society 2009, 131 (5) , 2029-2036. https://doi.org/10.1021/ja809125r
    80. Jian Yang, Peter S. White and Maurice Brookhart. Scope and Mechanism of the Iridium-Catalyzed Cleavage of Alkyl Ethers with Triethylsilane. Journal of the American Chemical Society 2008, 130 (51) , 17509-17518. https://doi.org/10.1021/ja806419h
    81. Victor Sumerin, Felix Schulz, Michiko Atsumi, Cong Wang, Martin Nieger, Markku Leskelä, Timo Repo, Pekka Pyykkö and Bernhard Rieger. Molecular Tweezers for Hydrogen: Synthesis, Characterization, and Reactivity. Journal of the American Chemical Society 2008, 130 (43) , 14117-14119. https://doi.org/10.1021/ja806627s
    82. Julian Chojnowski, Slawomir Rubinsztajn, Witold Fortuniak and Jan Kurjata . Synthesis of Highly Branched Alkoxysiloxane−Dimethylsiloxane Copolymers by Nonhydrolytic Dehydrocarbon Polycondensation Catalyzed by Tris(pentafluorophenyl)borane. Macromolecules 2008, 41 (20) , 7352-7358. https://doi.org/10.1021/ma801130y
    83. Gregory C. Welch, Thorsten Holtrichter-Roessmann and Douglas W. Stephan. Thermal Rearrangement of Phosphine−B(C6F5)3 Adducts. Inorganic Chemistry 2008, 47 (6) , 1904-1906. https://doi.org/10.1021/ic702485r
    84. Gregory C. Welch and, Douglas W. Stephan. Facile Heterolytic Cleavage of Dihydrogen by Phosphines and Boranes. Journal of the American Chemical Society 2007, 129 (7) , 1880-1881. https://doi.org/10.1021/ja067961j
    85. Lung Wa Chung,, Hung Gai Lee,, Zhenyang Lin, and, Yun-Dong Wu. Computational Study on the Reaction Mechanism of Hydrosilylation of Carbonyls Catalyzed by High-Valent Rhenium(V)−Di-oxo Complexes. The Journal of Organic Chemistry 2006, 71 (16) , 6000-6009. https://doi.org/10.1021/jo060654b
    86. Priyadarshine Hewavitharanage,, Evgeny O. Danilov, and, Douglas C. Neckers. Pentafluorophenyl Transfer:  A New Group-Transfer Reaction in Organoborate Salts. The Journal of Organic Chemistry 2005, 70 (26) , 10653-10659. https://doi.org/10.1021/jo050695s
    87. Julian Chojnowski,, Sławomir Rubinsztajn,, James A. Cella,, Witold Fortuniak,, Marek Cypryk,, Jan Kurjata, and, Krzysztof Kaźmierski. Mechanism of the B(C6F5)3-Catalyzed Reaction of Silyl Hydrides with Alkoxysilanes. Kinetic and Spectroscopic Studies. Organometallics 2005, 24 (25) , 6077-6084. https://doi.org/10.1021/om050563p
    88. Peter Shapland and, Edwin Vedejs. Intramolecular Hydroboration of Unsaturated Phosphine Boranes. The Journal of Organic Chemistry 2004, 69 (12) , 4094-4100. https://doi.org/10.1021/jo040125c
    89. Alexander D. Dilman and, Sema L. Ioffe. Carbon−Carbon Bond Forming Reactions Mediated by Silicon Lewis Acids. Chemical Reviews 2003, 103 (3) , 733-772. https://doi.org/10.1021/cr020003p
    90. James M. Blackwell,, Warren E. Piers,, Masood Parvez, and, Robert McDonald. Solution and Solid-State Characteristics of Imine Adducts with Tris(pentafluorophenyl)borane. Organometallics 2002, 21 (7) , 1400-1407. https://doi.org/10.1021/om011086n
    91. James M. Blackwell,, Warren E. Piers, and, Robert McDonald. Mechanistic Studies on the B(C6F5)3 Catalyzed Allylstannation of Aromatic Aldehydes with Ortho Donor Substituents. Journal of the American Chemical Society 2002, 124 (7) , 1295-1306. https://doi.org/10.1021/ja012028w
    92. Mamta Bhandari, Sandeep Rawat, Mandeep Kaur, Sanjay Singh. Catalytic Hydrosilylation of Imines by Aluminum Hydride Cations. European Journal of Organic Chemistry 2023, 26 (36) https://doi.org/10.1002/ejoc.202300674
    93. Zhenli Luo, Ji Yang, Zhen Yao, Jianbo Yang, Lijin Xu, Qian Shi. B(C 6 F 5 ) 3 ‐Catalyzed One‐Pot Tandem Diastereoselective Synthesis of cis ‐2,3‐Disubstituted 1,2,3,4‐Tetrahydroquinoxalines and cis ‐2,4‐Disubstituted 2,3,4,5‐Tetrahydro‐1 H ‐1,5‐benzodiazepines. Advanced Synthesis & Catalysis 2023, 39 https://doi.org/10.1002/adsc.202300817
    94. Jie Cui, Tongdao Wang. B(C 6 F 5 ) 3 -mediated direct intramolecular C7-alkenylation of N -propargylindoles. Chemical Communications 2023, 59 (68) , 10279-10282. https://doi.org/10.1039/D3CC02599C
    95. Zhenli Luo, Zhewei Li, Haoqiang Zhao, Ji Yang, Lijin Xu, Ming Lei, Qinghua Fan, Patrick J. Walsh. Borane‐Catalyzed Tandem Cyclization/Hydrosilylation Towards Enantio‐ and Diastereoselective Construction of trans ‐2,3‐Disubstituted‐1,2,3,4‐Tetrahydroquinoxalines. Angewandte Chemie 2023, 135 (32) https://doi.org/10.1002/ange.202305449
    96. Zhenli Luo, Zhewei Li, Haoqiang Zhao, Ji Yang, Lijin Xu, Ming Lei, Qinghua Fan, Patrick J. Walsh. Borane‐Catalyzed Tandem Cyclization/Hydrosilylation Towards Enantio‐ and Diastereoselective Construction of trans ‐2,3‐Disubstituted‐1,2,3,4‐Tetrahydroquinoxalines. Angewandte Chemie International Edition 2023, 62 (32) https://doi.org/10.1002/anie.202305449
    97. Chung Whan Lee, Haye Min Ko. Metal‐Free Catalytic Reduction of Amides: Recent Progress. Asian Journal of Organic Chemistry 2023, 12 (5) https://doi.org/10.1002/ajoc.202300098
    98. Feng Han, Guang-Sheng Lu, Dong-Ping Wu, Pei-Qiang Huang. Iridium and B(C6F5)3 co-catalyzed chemoselective deoxygenative reduction of tertiary amides: application to the efficient synthesis and late-stage modification of pharmaceuticals. Science China Chemistry 2023, 66 (4) , 1094-1100. https://doi.org/10.1007/s11426-022-1501-y
    99. Chijioke Kingsley Amadi, Ufuk Atamtürk, Andreas Lichtenberg, Aida Raauf, Sanjay Mathur. Undirected C-H Bond Activation in Aluminium Hydrido Enaminonates. Molecules 2023, 28 (5) , 2137. https://doi.org/10.3390/molecules28052137
    100. Idan Avigdori, Kuldeep Singh, Alla Pogoreltsev, Alexander Kaushansky, Natalia Fridman, Mark Gandelman. Nitrenium Salts in Intramolecular Lewis Pairs. Zeitschrift für anorganische und allgemeine Chemie 2023, 649 (4) https://doi.org/10.1002/zaac.202200326
    Load more citations

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect