logo

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2011, 133, 43, 17283-17295
RETURN TO ISSUEPREVArticleNEXT

Cobalt-Catalyzed, Room-Temperature Addition of Aromatic Imines to Alkynes via Directed C–H Bond Activation

View Author Information
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
[email protected]
Cite this: J. Am. Chem. Soc. 2011, 133, 43, 17283–17295
Publication Date (Web):September 28, 2011
https://doi.org/10.1021/ja2047073
Copyright © 2011 American Chemical Society
RIGHTS & PERMISSIONS
Article Views
8259
Altmetric
-
Citations
193
LEARN ABOUT THESE METRICS

Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.

Read OnlinePDF (2 MB)
Get e-Alerts
Supporting Info (1)»
SUBJECTS:

Abstract

Abstract Image

A quaternary catalytic system consisting of a cobalt salt, a triarylphosphine ligand, a Grignard reagent, and pyridine has been developed for chelation-assisted C–H bond activation of an aromatic imine, followed by insertion of an unactivated internal alkyne that occurs at ambient temperature. The reaction not only tolerates potentially senstitive functional groups (e.g., Cl, Br, CN, and tertiary amide), but also displays a unique regioselectivity. Thus, the presence of substituents such as methoxy, halogen, and cyano groups at the meta-position of the imino group led to selective C–C bond formation at the more sterically hindered ortho positions. Under acidic conditions, the hydroarylation products of dialkyl- and alkylarylacetylenes underwent cyclization to afford benzofulvene derivatives, while those of diarylacetylenes afforded the corresponding ketones in moderate to good yields. A mechanistic investigation into the reaction with the aid of deuterium-labeling experiments and kinetic analysis has indicated that oxidative addition of the ortho C–H bond is the rate-limiting step of the reaction. The kinetic analysis has also shed light on the complexity of the quaternary catalytic system.

Supporting Information

ARTICLE SECTIONS
Jump To

Experimental procedures and characterization of new compounds. 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 209 publications.

  1. Rong Chang, Yonglin Chen, Wenjing Yang, Zhuxia Zhang, Zhen Guo, Yanrong Li. Unveiling the Mechanism, Origin of Stereoselectivity, and Ligand-Dependent Reactivity in the Pd(II)-Catalyzed Unbiased Methylene C(sp3)–H Alkenylation–Aza-Wacker Cyclization Reaction. The Journal of Organic Chemistry 2020, 85 (20) , 13191-13203. https://doi.org/10.1021/acs.joc.0c01906
  2. Wenjing Li, Juan Tang, Shun Li, Xueli Zheng, Maolin Yuan, Bin Xu, Weidong Jiang, Haiyan Fu, Ruixiang Li, Hua Chen. Stereodivergent Synthesis of Alkenylpyridines via Pd/Cu Catalyzed C–H Alkenylation of Pyridinium Salts with Alkynes. Organic Letters 2020, 22 (20) , 7814-7819. https://doi.org/10.1021/acs.orglett.0c02679
  3. Chang-Sheng Wang, Sabrina Di Monaco, Anh Ngoc Thai, Md. Shafiqur Rahman, Benjamin Piaoxiang Pang, Chen Wang, Naohiko Yoshikai. Cobalt/Lewis Acid Catalysis for Hydrocarbofunctionalization of Alkynes via Cooperative C–H Activation. Journal of the American Chemical Society 2020, 142 (29) , 12878-12889. https://doi.org/10.1021/jacs.0c06412
  4. Benjamin A. Suslick, T. Don Tilley. Mechanistic Interrogation of Alkyne Hydroarylations Catalyzed by Highly Reduced, Single-Component Cobalt Complexes. Journal of the American Chemical Society 2020, 142 (25) , 11203-11218. https://doi.org/10.1021/jacs.0c04072
  5. Andrew Whyte, Alexa Torelli, Bijan Mirabi, Liher Prieto, José F. Rodríguez, Mark Lautens. Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes. Journal of the American Chemical Society 2020, 142 (20) , 9510-9517. https://doi.org/10.1021/jacs.0c03246
  6. Xiang-Ting Min, Ding-Wei Ji, Hao Zheng, Bing-Zhi Chen, Yan-Cheng Hu, Boshun Wan, Qing-An Chen. Cobalt-Catalyzed Regioselective Carboamidation of Alkynes with Imides Enabled by Cleavage of C–N and C–C Bonds. Organic Letters 2020, 22 (9) , 3386-3391. https://doi.org/10.1021/acs.orglett.0c00875
  7. Woohyeong Lee, Changhoon Shin, Soo Eun Park, Jung Min Joo. Regio- and Stereoselective Synthesis of Thiazole-Containing Triarylethylenes by Hydroarylation of Alkynes. The Journal of Organic Chemistry 2019, 84 (20) , 12913-12924. https://doi.org/10.1021/acs.joc.9b01619
  8. Ramón Azpíroz, Andrea Di Giuseppe, Asier Urriolabeitia, Vincenzo Passarelli, Victor Polo, Jesús J. Pérez-Torrente, Luis A. Oro, Ricardo Castarlenas. Hydride–Rhodium(III)-N-Heterocyclic Carbene Catalyst for Tandem Alkylation/Alkenylation via C–H Activation. ACS Catalysis 2019, 9 (10) , 9372-9386. https://doi.org/10.1021/acscatal.9b01233
  9. Bo Han, Pengchen Ma, Xuefeng Cong, Hui Chen, Xiaoming Zeng. Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study. Journal of the American Chemical Society 2019, 141 (22) , 9018-9026. https://doi.org/10.1021/jacs.9b03328
  10. Tian Yao, Kaifeng Du. Temperature-Controlled Mono- and Diolefination of Arene Using Rh(III)/RTIL as an Efficient and Recyclable Catalytic System. ACS Sustainable Chemistry & Engineering 2019, 7 (6) , 6068-6077. https://doi.org/10.1021/acssuschemeng.8b06262
  11. Wenying Ai, Rui Zhong, Xufang Liu, Qiang Liu. Hydride Transfer Reactions Catalyzed by Cobalt Complexes. Chemical Reviews 2019, 119 (4) , 2876-2953. https://doi.org/10.1021/acs.chemrev.8b00404
  12. Parthasarathy Gandeepan, Thomas Müller, Daniel Zell, Gianpiero Cera, Svenja Warratz, Lutz Ackermann. 3d Transition Metals for C–H Activation. Chemical Reviews 2019, 119 (4) , 2192-2452. https://doi.org/10.1021/acs.chemrev.8b00507
  13. Chen Zhang, Xiao-Mei Chen, Yi Luo, Jiang-Lian Li, Min Chen, Li Hai, Yong Wu. Imidazolium-Based Ionic Liquid: An Efficient, Normalized, and Recyclable Platform for Rh(III)-Catalyzed Directed C–H Carbenoid Coupling Reactions. ACS Sustainable Chemistry & Engineering 2018, 6 (10) , 13473-13479. https://doi.org/10.1021/acssuschemeng.8b03399
  14. Hanchao Cheng, José G. Hernández, and Carsten Bolm . Mechanochemical Ruthenium-Catalyzed Hydroarylations of Alkynes under Ball-Milling Conditions. Organic Letters 2017, 19 (23) , 6284-6287. https://doi.org/10.1021/acs.orglett.7b02973
  15. Ramasamy Manoharan and Masilamani Jeganmohan . Cobalt-Catalyzed Oxidative Cyclization of Benzamides with Maleimides: Synthesis of Isoindolone Spirosuccinimides. Organic Letters 2017, 19 (21) , 5884-5887. https://doi.org/10.1021/acs.orglett.7b02873
  16. Midori Nagamoto, Jun-ichi Fukuda, Miyuki Hatano, Hideki Yorimitsu, and Takahiro Nishimura . Hydroxoiridium-Catalyzed Hydroarylation of Alkynes and Bicycloalkenes with N-Sulfonylbenzamides. Organic Letters 2017, 19 (21) , 5952-5955. https://doi.org/10.1021/acs.orglett.7b02950
  17. Xuefeng Cong, Fei Fan, Pengchen Ma, Meiming Luo, Hui Chen, and Xiaoming Zeng . Low-Valent, High-Spin Chromium-Catalyzed Cleavage of Aromatic Carbon–Nitrogen Bonds at Room Temperature: A Combined Experimental and Theoretical Study. Journal of the American Chemical Society 2017, 139 (42) , 15182-15190. https://doi.org/10.1021/jacs.7b08579
  18. Shi-Yong Chen, Qingjiang Li, and Honggen Wang . Manganese(I)-Catalyzed Direct C–H Allylation of Arenes with Allenes. The Journal of Organic Chemistry 2017, 82 (20) , 11173-11181. https://doi.org/10.1021/acs.joc.7b02220
  19. Desaboini Nageswar Rao, Sk. Rasheed, Gaurav Raina, Qazi Naveed Ahmed, Chaitanya Kumar Jaladanki, Prasad V. Bharatam, and Parthasarathi Das . Cobalt-Catalyzed Regioselective Ortho C(sp2)-H Bond Nitration of Aromatics through Proton-Coupled Electron Transfer Assistance. The Journal of Organic Chemistry 2017, 82 (14) , 7234-7244. https://doi.org/10.1021/acs.joc.7b00808
  20. R. N. Prasad Tulichala, Mallepalli Shankar, and K. C. Kumara Swamy . Ruthenium-Catalyzed Oxidative Annulation and Hydroarylation of Chromene-3-carboxamides with Alkynes via Double C–H Functionalization. The Journal of Organic Chemistry 2017, 82 (10) , 5068-5079. https://doi.org/10.1021/acs.joc.7b00008
  21. Sachiyo Nakanowatari, Ruhuai Mei, Milica Feldt, and Lutz Ackermann . Cobalt(III)-Catalyzed Hydroarylation of Allenes via C–H Activation. ACS Catalysis 2017, 7 (4) , 2511-2515. https://doi.org/10.1021/acscatal.7b00207
  22. Zheng-Yang Gu, Cheng-Guo Liu, Shun-Yi Wang, and Shun-Jun Ji . Cobalt-Catalyzed Annulation of Amides with Isocyanides via C(sp2)–H Activation. The Journal of Organic Chemistry 2017, 82 (4) , 2223-2230. https://doi.org/10.1021/acs.joc.6b02797
  23. Sourav Sekhar Bera, Suvankar Debbarma, Avick Kumar Ghosh, Santanu Chand, and Modhu Sudan Maji . Cp*CoIII–Catalyzed syn-Selective C–H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks. The Journal of Organic Chemistry 2017, 82 (1) , 420-430. https://doi.org/10.1021/acs.joc.6b02516
  24. Michael J. Lopez, Ai Kondo, Haruki Nagae, Koji Yamamoto, Hayato Tsurugi, and Kazushi Mashima . C(sp3)–H Alkenylation Catalyzed by Cationic Alkylhafnium Complexes: Stereoselective Synthesis of Trisubstituted Alkenes from 2,6-Dimethylpyridines and Internal Alkynes. Organometallics 2016, 35 (22) , 3816-3827. https://doi.org/10.1021/acs.organomet.6b00655
  25. Vadim P. Boyarskiy, Dmitry S. Ryabukhin, Nadezhda A. Bokach, and Aleksander V. Vasilyev . Alkenylation of Arenes and Heteroarenes with Alkynes. Chemical Reviews 2016, 116 (10) , 5894-5986. https://doi.org/10.1021/acs.chemrev.5b00514
  26. Brendan J. Fallon, Etienne Derat, Muriel Amatore, Corinne Aubert, Fabrice Chemla, Franck Ferreira, Alejandro Perez-Luna, and Marc Petit . C2-Alkylation and Alkenylation of Indoles Catalyzed by a Low-Valent Cobalt Complex in the Absence of Reductant. Organic Letters 2016, 18 (9) , 2292-2295. https://doi.org/10.1021/acs.orglett.6b00939
  27. Malay Sen, Balakumar Emayavaramban, Nagaraju Barsu, J. Richard Premkumar, and Basker Sundararaju . Cp*Co(III)-Catalyzed C(sp3)–H Bond Activation: A Highly Stereoselective and Regioselective Alkenylation of 8-Methylquinoline with Alkynes. ACS Catalysis 2016, 6 (5) , 2792-2796. https://doi.org/10.1021/acscatal.6b00612
  28. Vinod G. Landge, Garima Jaiswal, and Ekambaram Balaraman . Cobalt-Catalyzed Bis-alkynylation of Amides via Double C–H Bond Activation. Organic Letters 2016, 18 (4) , 812-815. https://doi.org/10.1021/acs.orglett.6b00095
  29. Marc Moselage, Jie Li, and Lutz Ackermann . Cobalt-Catalyzed C–H Activation. ACS Catalysis 2016, 6 (2) , 498-525. https://doi.org/10.1021/acscatal.5b02344
  30. Tung Thanh Nguyen, Liene Grigorjeva, and Olafs Daugulis . Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp2 C–H Bonds. ACS Catalysis 2016, 6 (2) , 551-554. https://doi.org/10.1021/acscatal.5b02391
  31. Fanyang Mo, Hee Nam Lim, and Guangbin Dong . Bifunctional Ligand-Assisted Catalytic Ketone α-Alkenylation with Internal Alkynes: Controlled Synthesis of Enones and Mechanistic Studies. Journal of the American Chemical Society 2015, 137 (49) , 15518-15527. https://doi.org/10.1021/jacs.5b10466
  32. Jitan Zhang, Hui Chen, Cong Lin, Zhanxiang Liu, Chen Wang, and Yuhong Zhang . Cobalt-Catalyzed Cyclization of Aliphatic Amides and Terminal Alkynes with Silver-Cocatalyst. Journal of the American Chemical Society 2015, 137 (40) , 12990-12996. https://doi.org/10.1021/jacs.5b07424
  33. Wengang Xu, Rupankar Paira, and Naohiko Yoshikai . Ortho-C–H Benzylation of Aryl Imines with Benzyl Phosphates under Cobalt–Pyphos Catalysis. Organic Letters 2015, 17 (17) , 4192-4195. https://doi.org/10.1021/acs.orglett.5b01955
  34. Yanfeng Dang, Shuanglin Qu, Yuan Tao, Xi Deng, and Zhi-Xiang Wang . Mechanistic Insight into Ketone α-Alkylation with Unactivated Olefins via C–H Activation Promoted by Metal–Organic Cooperative Catalysis (MOCC): Enriching the MOCC Chemistry. Journal of the American Chemical Society 2015, 137 (19) , 6279-6291. https://doi.org/10.1021/jacs.5b01502
  35. Yiyang Ma, Dongchao Zhang, Zhiyuan Yan, Mengfan Wang, Changliang Bian, Xinlong Gao, Emilio E. Bunel, and Aiwen Lei . Iron-Catalyzed Oxidative C–H/C–H Cross-Coupling between Electron-Rich Arenes and Alkenes. Organic Letters 2015, 17 (9) , 2174-2177. https://doi.org/10.1021/acs.orglett.5b00775
  36. Wenbo Ma and Lutz Ackermann . Cobalt(II)-Catalyzed Oxidative C–H Alkenylations: Regio- and Site-Selective Access to Isoindolin-1-one. ACS Catalysis 2015, 5 (5) , 2822-2825. https://doi.org/10.1021/acscatal.5b00322
  37. Brendan J. Fallon, Etienne Derat, Muriel Amatore, Corinne Aubert, Fabrice Chemla, Franck Ferreira, Alejandro Perez-Luna, and Marc Petit . C–H Activation/Functionalization Catalyzed by Simple, Well-Defined Low-Valent Cobalt Complexes. Journal of the American Chemical Society 2015, 137 (7) , 2448-2451. https://doi.org/10.1021/ja512728f
  38. Mun Yee Wong, Takeshi Yamakawa, and Naohiko Yoshikai . Iron-Catalyzed Directed C2-Alkylation and Alkenylation of Indole with Vinylarenes and Alkynes. Organic Letters 2015, 17 (3) , 442-445. https://doi.org/10.1021/ol503395g
  39. Manash Kumar Manna, Asik Hossian, and Ranjan Jana . Merging C–H Activation and Alkene Difunctionalization at Room Temperature: A Palladium-Catalyzed Divergent Synthesis of Indoles and Indolines. Organic Letters 2015, 17 (3) , 672-675. https://doi.org/10.1021/ol5036968
  40. Joshua R. Hummel and Jonathan A. Ellman . Cobalt(III)-Catalyzed Synthesis of Indazoles and Furans by C–H Bond Functionalization/Addition/Cyclization Cascades. Journal of the American Chemical Society 2015, 137 (1) , 490-498. https://doi.org/10.1021/ja5116452
  41. Da-Gang Yu, Tobias Gensch, Francisco de Azambuja, Suhelen Vásquez-Céspedes, and Frank Glorius . Co(III)-Catalyzed C–H Activation/Formal SN-Type Reactions: Selective and Efficient Cyanation, Halogenation, and Allylation. Journal of the American Chemical Society 2014, 136 (51) , 17722-17725. https://doi.org/10.1021/ja511011m
  42. Boris Vabre, Félix Deschamps, and Davit Zargarian . Ortho Derivatization of Phenols through C–H Nickelation: Synthesis, Characterization, and Reactivities of Ortho-Nickelated Phosphinite Complexes. Organometallics 2014, 33 (22) , 6623-6632. https://doi.org/10.1021/om500938u
  43. Lutz Ackermann . Cobalt-Catalyzed C–H Arylations, Benzylations, and Alkylations with Organic Electrophiles and Beyond. The Journal of Organic Chemistry 2014, 79 (19) , 8948-8954. https://doi.org/10.1021/jo501361k
  44. Olesya M. Kuzmina and Paul Knochel . Room-Temperature Chromium(II)-Catalyzed Direct Arylation of Pyridines, Aryl Oxazolines, and Imines Using Arylmagnesium Reagents. Organic Letters 2014, 16 (19) , 5208-5211. https://doi.org/10.1021/ol502623v
  45. Giacomo E. M. Crisenza, Niall G. McCreanor, and John F. Bower . Branch-Selective, Iridium-Catalyzed Hydroarylation of Monosubstituted Alkenes via a Cooperative Destabilization Strategy. Journal of the American Chemical Society 2014, 136 (29) , 10258-10261. https://doi.org/10.1021/ja505776m
  46. Christine Hahn, Mayra Miranda, Nagendra P. B. Chittineni, Trent A. Pinion, and Ricardo Perez . Mechanistic Studies on Platinum(II) Catalyzed Hydroarylation of Alkynes. Organometallics 2014, 33 (12) , 3040-3050. https://doi.org/10.1021/om5003123
  47. Ke Gao and Naohiko Yoshikai . Low-Valent Cobalt Catalysis: New Opportunities for C–H Functionalization. Accounts of Chemical Research 2014, 47 (4) , 1208-1219. https://doi.org/10.1021/ar400270x
  48. Hélène Pellissier and Hervé Clavier . Enantioselective Cobalt-Catalyzed Transformations. Chemical Reviews 2014, 114 (5) , 2775-2823. https://doi.org/10.1021/cr4004055
  49. Xiao-Cheng Huang, Xu-Heng Yang, Ren-Jie Song, and Jin-Heng Li . Rhodium-Catalyzed Synthesis of Isoquinolines and Indenes from Benzylidenehydrazones and Internal Alkynes. The Journal of Organic Chemistry 2014, 79 (3) , 1025-1031. https://doi.org/10.1021/jo402497v
  50. Rajendran Manikandan and Masilamani Jeganmohan . Ruthenium-Catalyzed Hydroarylation of Anilides with Alkynes: An Efficient Route to Ortho-Alkenylated Anilines. Organic Letters 2014, 16 (3) , 912-915. https://doi.org/10.1021/ol403666s
  51. Yohei Ogiwara, Masaru Tamura, Takuya Kochi, Yusuke Matsuura, Naoto Chatani, and Fumitoshi Kakiuchi . Ruthenium-Catalyzed Ortho-Selective C–H Alkenylation of Aromatic Compounds with Alkenyl Esters and Ethers. Organometallics 2014, 33 (1) , 402-420. https://doi.org/10.1021/om401204h
  52. Gyeongshin Choi, Hayato Tsurugi, and Kazushi Mashima . Hemilabile N-Xylyl-N′-methylperimidine Carbene Iridium Complexes as Catalysts for C–H Activation and Dehydrogenative Silylation: Dual Role of N-Xylyl Moiety for ortho-C–H Bond Activation and Reductive Bond Cleavage. Journal of the American Chemical Society 2013, 135 (35) , 13149-13161. https://doi.org/10.1021/ja406519u
  53. Tetsuya Sakurada, Yu-ki Sugiyama, and Sentaro Okamoto . Cobalt-Catalyzed Cross Addition of Silylacetylenes to Internal Alkynes. The Journal of Organic Chemistry 2013, 78 (8) , 3583-3591. https://doi.org/10.1021/jo400064b
  54. Fernando Hung-Low and Christopher A. Bradley . Synthesis of a Bis(indenyl) Co(I) Anion: A Reactive Source of a 14 Electron Indenyl Co(I) Equivalent. Inorganic Chemistry 2013, 52 (5) , 2446-2457. https://doi.org/10.1021/ic302320w
  55. David G. Johnson, Jason M. Lynam, Neetisha S. Mistry, John M. Slattery, Robert J. Thatcher, and Adrian C. Whitwood . Ruthenium-Mediated C–H Functionalization of Pyridine: The Role of Vinylidene and Pyridylidene Ligands. Journal of the American Chemical Society 2013, 135 (6) , 2222-2234. https://doi.org/10.1021/ja3097256
  56. Yuto Hashimoto, Koji Hirano, Tetsuya Satoh, Fumitoshi Kakiuchi, and Masahiro Miura . Regioselective C–H Bond Cleavage/Alkyne Insertion under Ruthenium Catalysis. The Journal of Organic Chemistry 2013, 78 (2) , 638-646. https://doi.org/10.1021/jo3025237
  57. Takeshi Yamakawa and Naohiko Yoshikai . Annulation of α,β-Unsaturated Imines and Alkynes via Cobalt-Catalyzed Olefinic C–H Activation. Organic Letters 2013, 15 (1) , 196-199. https://doi.org/10.1021/ol303259m
  58. Peng Zhao, Fen Wang, Keli Han, and Xingwei Li . Ruthenium- and Sulfonamide-Catalyzed Cyclization between N-Sulfonyl Imines and Alkynes. Organic Letters 2012, 14 (21) , 5506-5509. https://doi.org/10.1021/ol302594w
  59. Jaesung Kwak, Youhwa Ohk, Yousung Jung, and Sukbok Chang . Rollover Cyclometalation Pathway in Rhodium Catalysis: Dramatic NHC Effects in the C–H Bond Functionalization. Journal of the American Chemical Society 2012, 134 (42) , 17778-17788. https://doi.org/10.1021/ja308205d
  60. Ke Gao, Pin-Sheng Lee, Chong Long, and Naohiko Yoshikai . Cobalt-Catalyzed Ortho-Arylation of Aromatic Imines with Aryl Chlorides. Organic Letters 2012, 14 (16) , 4234-4237. https://doi.org/10.1021/ol301934y
  61. Qian Li and Zhi-Xiang Yu . Density Functional Theory Study of the Mechanism of the Rhodium(I)-Catalyzed Conjugated Diene Assisted Allylic C–H Bond Activation and Addition to Alkenes Using Ene-2-dienes As Substrates. Organometallics 2012, 31 (14) , 5185-5195. https://doi.org/10.1021/om300523u
  62. Rong Zeng, Chunling Fu, and Shengming Ma . Highly Selective Mild Stepwise Allylation of N-Methoxybenzamides with Allenes. Journal of the American Chemical Society 2012, 134 (23) , 9597-9600. https://doi.org/10.1021/ja303790s
  63. Ye Wei, Indubhusan Deb, and Naohiko Yoshikai . Palladium-Catalyzed Aerobic Oxidative Cyclization of N-Aryl Imines: Indole Synthesis from Anilines and Ketones. Journal of the American Chemical Society 2012, 134 (22) , 9098-9101. https://doi.org/10.1021/ja3030824
  64. Yuto Hashimoto, Koji Hirano, Tetsuya Satoh, Fumitoshi Kakiuchi, and Masahiro Miura . Ruthenium(II)-Catalyzed Regio- and Stereoselective Hydroarylation of Alkynes via Directed C–H Functionalization. Organic Letters 2012, 14 (8) , 2058-2061. https://doi.org/10.1021/ol300579m
  65. Anup Mandal, Bholanath Garai, Suman Dana, Ratnadeep Bera, Mahiuddin Baidya. Cross‐Dehydrogenative Coupling/Annulation of Arene Carboxylic Acids and Alkenes in Water with Ruthenium(II) Catalyst and Air. Chemistry – An Asian Journal 2020, 15 (23) , 4009-4013. https://doi.org/10.1002/asia.202001087
  66. Yuan Gao, Mengfan Zhang, Chaoyu Wang, Zhen Yang, Xianqiang Huang, Ruokun Feng, Chenze Qi. Cobalt( ii )-catalyzed hydroarylation of 1,3-diynes and internal alkynes with picolinamides promoted by alcohol. Chemical Communications 2020, 56 (91) , 14231-14234. https://doi.org/10.1039/D0CC05616B
  67. David F. Fernández, José L. Mascareñas, Fernando López. Catalytic addition of C–H bonds across C–C unsaturated systems promoted by iridium( i ) and its group IX congeners. Chemical Society Reviews 2020, 49 (20) , 7378-7405. https://doi.org/10.1039/D0CS00359J
  68. David Zanders, Goran Bačić, Dominique Leckie, Oluwadamilola Odegbesan, Jeremy Rawson, Jason D. Masuda, Anjana Devi, Seán T. Barry. Ein seltenes Low‐Spin‐Co IV ‐Bis(β‐silyldiamid) mit hoher thermischer Stabilität: Sterische Erzwingung einer Dublettkonfiguration. Angewandte Chemie 2020, 132 (33) , 14242-14246. https://doi.org/10.1002/ange.202001518
  69. David Zanders, Goran Bačić, Dominique Leckie, Oluwadamilola Odegbesan, Jeremy Rawson, Jason D. Masuda, Anjana Devi, Seán T. Barry. A Rare Low‐Spin Co IV Bis(β‐silyldiamide) with High Thermal Stability: Steric Enforcement of a Doublet Configuration. Angewandte Chemie International Edition 2020, 59 (33) , 14138-14142. https://doi.org/10.1002/anie.202001518
  70. Naohiko Yoshikai. Cobalt‐Catalysed C–H Functionalisation. 2020,,, 89-161. https://doi.org/10.1002/9783527814855.ch4
  71. , . Cobalt Catalysis in Organic Synthesis. 2020,,https://doi.org/10.1002/9783527814855
  72. Kaifeng Du, Tian Yao. The C–H activated controlled mono- and di-olefination of arenes in ionic liquids at room temperature. RSC Advances 2020, 10 (6) , 3203-3211. https://doi.org/10.1039/C9RA09736H
  73. Abdol R. Hajipour, Zahra Khorsandi. Cobalt-catalyzed C H activation/C O formation: Synthesis of benzofuranones. Tetrahedron Letters 2020, 61 (3) , 151396. https://doi.org/10.1016/j.tetlet.2019.151396
  74. Dingyi Wang, Ben Dong, Yandong Wang, Jiasheng Qian, Jinjun Zhu, Yue Zhao, Zhuangzhi Shi. Rhodium-catalysed direct hydroarylation of alkenes and alkynes with phosphines through phosphorous-assisted C−H activation. Nature Communications 2019, 10 (1) https://doi.org/10.1038/s41467-019-11420-5
  75. Parthasarathy Gandeepan, Lutz Ackermann. Diastereoselective Formation of Alkenes Through C ( sp 2 ) H Bond Activation. 2019,,, 239-274. https://doi.org/10.1002/9783527810857.ch9
  76. , . C‐H Activation for Asymmetric Synthesis. 2019,,https://doi.org/10.1002/9783527810857
  77. Cong Lin, Liang Shen. Co-catalyzed ortho -C–H functionalization/annulation of arenes and alkenes with alkynylsilanes: access to isoquinolone and pyridone motifs. RSC Advances 2019, 9 (53) , 30650-30654. https://doi.org/10.1039/C9RA06963A
  78. Qin Xiong, Haohua Chen, Tao Zhang, Chunhui Shan, Ruopeng Bai, Yu Lan. On the Mechanism of Palladium‐Catalyzed Unsaturated Bond Transformations: A Review of Theoretical Studies. Asian Journal of Organic Chemistry 2019, 8 (8) , 1194-1206. https://doi.org/10.1002/ajoc.201900314
  79. Anil Kumar, Nachimuthu Muniraj, Kandikere Ramaiah Prabhu. Cobalt(III)-Catalyzed Direct ortho -Alkenylation of Arylpyrazoles: A Comparative Study on Decarboxylation and Desilylation. European Journal of Organic Chemistry 2019, 2019 (16) , 2735-2739. https://doi.org/10.1002/ejoc.201900270
  80. Friedrich Kreyenschmidt, Selim E. Meurer, Konrad Koszinowski. Mechanisms of Cobalt/Phosphine‐Catalyzed Cross‐Coupling Reactions. Chemistry – A European Journal 2019, 25 (23) , 5912-5921. https://doi.org/10.1002/chem.201805964
  81. Adán B. González-Pérez, Pedro Villar, Angel R. de Lera. A Computational Study of Model Parent Systems and Reported Aza-(Iso)Nazarov/Aza-(Iso)Piancatelli Electrocyclic Reactions. European Journal of Organic Chemistry 2019, 2019 (14) , 2539-2551. https://doi.org/10.1002/ejoc.201900103
  82. Yuanyuan Hu, Congyang Wang. Manganese-Catalyzed C−H Olefination Reactions. ChemCatChem 2019, 11 (4) , 1167-1174. https://doi.org/10.1002/cctc.201801787
  83. Yu-Che Chang, Sekar Prakash, Chien-Hong Cheng. Re I -Catalyzed highly regio- and stereoselective C–H addition to terminal and internal alkynes. Organic Chemistry Frontiers 2019, 6 (4) , 432-436. https://doi.org/10.1039/C8QO01068D
  84. Oriol Planas, Christopher J. Whiteoak, Xavi Ribas. Recent Advances in Cobalt-Catalyzed Cross-coupling Reactions. 2018,,, 297-328. https://doi.org/10.1002/9783527699087.ch12
  85. , . Non-Noble Metal Catalysis. 2019,,https://doi.org/10.1002/9783527699087
  86. Parthasarathy Gandeepan, Lutz Ackermann. Organometallic Chelation-Assisted C−H Functionalization. 2018,,, 391-423. https://doi.org/10.1002/9783527699087.ch15
  87. , . Non-Noble Metal Catalysis. 2019,,https://doi.org/10.1002/9783527699087
  88. Zhen Li, Wei‐Liang Duan. Palladium‐Catalyzed C−H Alkenylation of Arenes with Alkynes: Stereoselective Synthesis of Vinyl Chlorides via a 1,4‐Chlorine Migration. Angewandte Chemie 2018, 130 (49) , 16273-16277. https://doi.org/10.1002/ange.201808866
  89. Zhen Li, Wei‐Liang Duan. Palladium‐Catalyzed C−H Alkenylation of Arenes with Alkynes: Stereoselective Synthesis of Vinyl Chlorides via a 1,4‐Chlorine Migration. Angewandte Chemie International Edition 2018, 57 (49) , 16041-16045. https://doi.org/10.1002/anie.201808866
  90. Yang Li, Silong Xu. Transition-Metal-Catalyzed C−H Functionalization for Construction of Quaternary Carbon Centers. Chemistry - A European Journal 2018, 24 (61) , 16218-16245. https://doi.org/10.1002/chem.201800921
  91. Daniel Gallego, Edwin A. Baquero. Recent Advances on Mechanistic Studies on C–H Activation Catalyzed by Base Metals. Open Chemistry 2018, 16 (1) , 1001-1058. https://doi.org/10.1515/chem-2018-0102
  92. Chengming Wang, Magnus Rueping. Rhenium- and Manganese-Catalyzed Selective Alkenylation of Indoles. ChemCatChem 2018, 10 (12) , 2681-2685. https://doi.org/10.1002/cctc.201800553
  93. Richard C. Larock, Li Zhang. Formation of Alkanes and Arenes by Ring-forming Reactions. 2018,,, 1-111. https://doi.org/10.1002/9781118662083.cot01-004
  94. Richard C. Larock. Comprehensive Organic Transformations. 2018,,https://doi.org/
  95. Cong Lin, Zhengkai Chen, Zhanxiang Liu, Yuhong Zhang. Direct ortho -Acyloxylation of Arenes and Alkenes by Cobalt Catalysis. Advanced Synthesis & Catalysis 2018, 360 (3) , 519-532. https://doi.org/10.1002/adsc.201701144
  96. Oriol Planas, Paula G. Chirila, Christopher J. Whiteoak, Xavi Ribas. Current Mechanistic Understanding of Cobalt-Catalyzed C–H Functionalization. 2018,,, 209-282. https://doi.org/10.1016/bs.adomc.2018.02.002
  97. . . 2018,,https://doi.org/
  98. Rajagopal Santhoshkumar, Chien-Hong Cheng. Hydroarylations by cobalt-catalyzed C–H activation. Beilstein Journal of Organic Chemistry 2018, 14 , 2266-2288. https://doi.org/10.3762/bjoc.14.202
  99. Pin-Sheng Lee, Wengang Xu, Naohiko Yoshikai. Directed C-H Alkenylation of Aryl Imines with Alkenyl Phosphates Promoted by a Cobalt-N-Heterocyclic Carbene Catalyst. Advanced Synthesis & Catalysis 2017, 359 (24) , 4340-4347. https://doi.org/10.1002/adsc.201701105
  100. Pedro Villuendas, Sara Ruiz, Esteban P. Urriolabeitia. Functionalization of Heteroaromatic Substrates using Groups 9 and 10 Catalysts. 2017,,, 5-47. https://doi.org/10.1002/9783527697649.ch1

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.

OOPS

You have to login with your ACS ID befor you can login with your Mendeley account.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE