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Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes

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Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States
Cite this: J. Am. Chem. Soc. 2013, 135, 4, 1585–1592
Publication Date (Web):January 14, 2013
https://doi.org/10.1021/ja3116718
Copyright © 2013 American Chemical Society
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Abstract

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The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy2Ph)2Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for the Mizoroki–Heck-type, room temperature, internally selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the benchtop with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield.

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Experimental procedures and spectral data (1H, 13C, 31P as applicable) for all new compounds and X-ray crystallographic data (CIF) for complexes 1 and 4. This material is available free of charge via the Internet at http://pubs.acs.org.

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  7. Yunlong Li, Haibo Liu, Zilong Huang, Yuan He, Bao-Hua Xu, Hongmei Wang, Zhengkun Yu. Visible-Light-Driven, Palladium-Catalyzed Heck Reaction of Internal Vinyl Bromides with Styrenes. The Journal of Organic Chemistry 2021, 86 (12) , 8402-8413. https://doi.org/10.1021/acs.joc.1c00838
  8. Yorck Mohr, Marcelo Alves-Favaro, Rémy Rajapaksha, Gaëlle Hisler, Alisa Ranscht, Partha Samanta, Chantal Lorentz, Mathis Duguet, Caroline Mellot-Draznieks, Elsje Alessandra Quadrelli, Florian M. Wisser, Jérôme Canivet. Heterogenization of a Molecular Ni Catalyst within a Porous Macroligand for the Direct C–H Arylation of Heteroarenes. ACS Catalysis 2021, 11 (6) , 3507-3515. https://doi.org/10.1021/acscatal.1c00209
  9. Zhen Wang, Yuanyuan Hu, Hongwei Jin, Yunkui Liu, Bingwei Zhou. Nickel-Catalyzed Arylation/Alkenylation of tert-Cyclobutanols with Aryl/Alkenyl Triflates via a C–C Bond Cleavage. The Journal of Organic Chemistry 2021, 86 (1) , 466-474. https://doi.org/10.1021/acs.joc.0c02209
  10. Alexandre J. Sicard, R. Tom Baker. Safe and Expeditious Preparation of Ni(cod)2 for Same-Day High-Throughput Screening. Organic Process Research & Development 2020, 24 (12) , 2950-2952. https://doi.org/10.1021/acs.oprd.0c00435
  11. Timothy B. Boit, Ana S. Bulger, Jacob E. Dander, Neil K. Garg. Activation of C–O and C–N Bonds Using Non-Precious-Metal Catalysis. ACS Catalysis 2020, 10 (20) , 12109-12126. https://doi.org/10.1021/acscatal.0c03334
  12. Lukas Nattmann, Josep Cornella. Ni(4-tBustb)3: A Robust 16-Electron Ni(0) Olefin Complex for Catalysis. Organometallics 2020, 39 (18) , 3295-3300. https://doi.org/10.1021/acs.organomet.0c00485
  13. Yi Deng, Chunyang Zhao, Yu Zhou, Hongwei Wang, Xuexiang Li, Gui-Juan Cheng, Junkai Fu. Directing-Group-Based Strategy Enabling Intermolecular Heck-Type Reaction of Cycloketone Oxime Esters and Unactivated Alkenes. Organic Letters 2020, 22 (9) , 3524-3530. https://doi.org/10.1021/acs.orglett.0c00963
  14. Richard Y. Liu, Joseph M. Dennis, Stephen L. Buchwald. The Quest for the Ideal Base: Rational Design of a Nickel Precatalyst Enables Mild, Homogeneous C–N Cross-Coupling. Journal of the American Chemical Society 2020, 142 (9) , 4500-4507. https://doi.org/10.1021/jacs.0c00286
  15. Jiyao Han, Xiaowei Sun, Xiao Wang, Qiong Wang, Shenghuai Hou, Xin Song, Yingqin Wei, Rongyu Wang, Wenhua Ji. Covalent Organic Framework as a Heterogeneous Ligand for the Regioselective Oxidative Heck Reaction. Organic Letters 2020, 22 (4) , 1480-1484. https://doi.org/10.1021/acs.orglett.0c00061
  16. Jeremy Duczynski, Alexandre N. Sobolev, Stephen A. Moggach, Reto Dorta, Scott G. Stewart. The Synthesis and Catalytic Activity of New Mixed NHC-Phosphite Nickel(0) Complexes. Organometallics 2020, 39 (1) , 105-115. https://doi.org/10.1021/acs.organomet.9b00672
  17. Milauni M. Mehta, Timothy B. Boit, Jacob E. Dander, Neil K. Garg. Ni-Catalyzed Suzuki–Miyaura Cross-Coupling of Aliphatic Amides on the Benchtop. Organic Letters 2020, 22 (1) , 1-5. https://doi.org/10.1021/acs.orglett.9b03434
  18. Dan Ba, Yanhui Chen, Weiwei Lv, Si Wen, Guolin Cheng. Copper-Catalyzed Three-Component Cascade Michael Addition/Heck-Type Alkylation/Annulation: Accessing Fully Substituted 1,3-Dihydro-2H-pyrrol-2-ones. Organic Letters 2019, 21 (21) , 8603-8606. https://doi.org/10.1021/acs.orglett.9b03189
  19. E. Ryan Barber, Hannah M. Hynds, Claudia P. Stephens, Holli E. Lemons, Emily T. Fredrickson, Dale J. Wilger. Nickel-Catalyzed Hydroarylation of Alkynes under Reductive Conditions with Aryl Bromides and Water. The Journal of Organic Chemistry 2019, 84 (18) , 11612-11622. https://doi.org/10.1021/acs.joc.9b01556
  20. Feiyan Yang, Youxiang Jin, Chuan Wang. Nickel-Catalyzed Asymmetric Intramolecular Reductive Heck Reaction of Unactivated Alkenes. Organic Letters 2019, 21 (17) , 6989-6994. https://doi.org/10.1021/acs.orglett.9b02577
  21. Guo-Ming Ho, Heiko Sommer, Ilan Marek. Highly E-Selective, Stereoconvergent Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkenyl Ethers. Organic Letters 2019, 21 (8) , 2913-2917. https://doi.org/10.1021/acs.orglett.9b00946
  22. Hui Jiang, Sheng-Chun Sha, Soo A Jeong, Brian C. Manor, Patrick J. Walsh. Ni(NIXANTPHOS)-Catalyzed Mono-Arylation of Toluenes with Aryl Chlorides and Bromides. Organic Letters 2019, 21 (6) , 1735-1739. https://doi.org/10.1021/acs.orglett.9b00294
  23. Konstantinos D. Vogiatzis, Mikhail V. Polynski, Justin K. Kirkland, Jacob Townsend, Ali Hashemi, Chong Liu, Evgeny A. Pidko. Computational Approach to Molecular Catalysis by 3d Transition Metals: Challenges and Opportunities. Chemical Reviews 2019, 119 (4) , 2453-2523. https://doi.org/10.1021/acs.chemrev.8b00361
  24. Jillian S. K. Clark, Ryan T. McGuire, Christopher M. Lavoie, Michael J. Ferguson, Mark Stradiotto. Examining the Impact of Heteroaryl Variants of PAd-DalPhos on Nickel-Catalyzed C(sp2)-N Cross-Couplings. Organometallics 2019, 38 (1) , 167-175. https://doi.org/10.1021/acs.organomet.8b00451
  25. Chunlin Tang, Ran Zhang, Bo Zhu, Junkai Fu, Yi Deng, Li Tian, Wei Guan, Xihe Bi. Directed Copper-Catalyzed Intermolecular Heck-Type Reaction of Unactivated Olefins and Alkyl Halides. Journal of the American Chemical Society 2018, 140 (49) , 16929-16935. https://doi.org/10.1021/jacs.8b10874
  26. Hui Yu, Bin Hu, Hanmin Huang. Nickel-Catalyzed Benzylation of Aryl Alkenes with Benzylamines via C–N Bond Activation. The Journal of Organic Chemistry 2018, 83 (22) , 13922-13929. https://doi.org/10.1021/acs.joc.8b02279
  27. Megan Mohadjer Beromi, Gourab Banerjee, Gary W. Brudvig, David J. Charboneau, Nilay Hazari, Hannah M. C. Lant, Brandon Q. Mercado. Modifications to the Aryl Group of dppf-Ligated Ni σ-Aryl Precatalysts: Impact on Speciation and Catalytic Activity in Suzuki–Miyaura Coupling Reactions. Organometallics 2018, 37 (21) , 3943-3955. https://doi.org/10.1021/acs.organomet.8b00589
  28. Christopher M. Lavoie, Joseph P. Tassone, Michael J. Ferguson, Yuqiao Zhou, Erin R. Johnson, Mark Stradiotto. Probing the Influence of PAd-DalPhos Ancillary Ligand Structure on Nickel-Catalyzed Ammonia Cross-Coupling. Organometallics 2018, 37 (21) , 4015-4023. https://doi.org/10.1021/acs.organomet.8b00605
  29. Y. Yang, A. C. Reber, S. E. Gilliland, III, C. E. Castano, B. F. Gupton, S. N. Khanna. Donor/Acceptor Concepts for Developing Efficient Suzuki Cross-Coupling Catalysts Using Graphene-Supported Ni, Cu, Fe, Pd, and Bimetallic Pd/Ni Clusters. The Journal of Physical Chemistry C 2018, 122 (44) , 25396-25403. https://doi.org/10.1021/acs.jpcc.8b07538
  30. Sophia L. Shevick, Carla Obradors, Ryan A. Shenvi. Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation. Journal of the American Chemical Society 2018, 140 (38) , 12056-12068. https://doi.org/10.1021/jacs.8b06458
  31. Hyung Yoon, Austin D. Marchese, Mark Lautens. Carboiodination Catalyzed by Nickel. Journal of the American Chemical Society 2018, 140 (35) , 10950-10954. https://doi.org/10.1021/jacs.8b06966
  32. Jessica M. Weber, Ashley R. Longstreet, Timothy F. Jamison. Bench-Stable Nickel Precatalysts with Heck-type Activation. Organometallics 2018, 37 (16) , 2716-2722. https://doi.org/10.1021/acs.organomet.8b00351
  33. Alex J. Nett, Santiago Cañellas, Yuki Higuchi, Michael T. Robo, Jeanne M. Kochkodan, M. Taylor Haynes, II, Jeff W. Kampf, John Montgomery. Stable, Well-Defined Nickel(0) Catalysts for Catalytic C–C and C–N Bond Formation. ACS Catalysis 2018, 8 (7) , 6606-6611. https://doi.org/10.1021/acscatal.8b02187
  34. Alexandre V. Gatien, Christopher M. Lavoie, Raymond N. Bennett, Michael J. Ferguson, Robert McDonald, Erin R. Johnson, Alexander W. H. Speed, Mark Stradiotto. Application of Diazaphospholidine/Diazaphospholene-Based Bisphosphines in Room-Temperature Nickel-Catalyzed C(sp2)–N Cross-Couplings of Primary Alkylamines with (Hetero)aryl Chlorides and Bromides. ACS Catalysis 2018, 8 (6) , 5328-5339. https://doi.org/10.1021/acscatal.8b01005
  35. Yuxiu Li, Kuai Wang, Yuanyuan Ping, Yifan Wang, and Wangqing Kong . Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles. Organic Letters 2018, 20 (4) , 921-924. https://doi.org/10.1021/acs.orglett.7b03713
  36. Kieran D. Jones, Dennis J. Power, Donald Bierer, Kersten M. Gericke, and Scott G. Stewart . Nickel Phosphite/Phosphine-Catalyzed C–S Cross-Coupling of Aryl Chlorides and Thiols. Organic Letters 2018, 20 (1) , 208-211. https://doi.org/10.1021/acs.orglett.7b03560
  37. Tannaz Ebrahimi, Dinesh C. Aluthge, Brian O. Patrick, Savvas G. Hatzikiriakos, and Parisa Mehrkhodavandi . Air- and Moisture-Stable Indium Salan Catalysts for Living Multiblock PLA Formation in Air. ACS Catalysis 2017, 7 (10) , 6413-6418. https://doi.org/10.1021/acscatal.7b01939
  38. Alex J. Nett, John Montgomery, and Paul M. Zimmerman . Entrances, Traps, and Rate-Controlling Factors for Nickel-Catalyzed C–H Functionalization. ACS Catalysis 2017, 7 (10) , 7352-7362. https://doi.org/10.1021/acscatal.7b02919
  39. Bijay Shrestha, Prakash Basnet, Roshan K. Dhungana, Shekhar KC, Surendra Thapa, Jeremiah M. Sears, and Ramesh Giri . Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles. Journal of the American Chemical Society 2017, 139 (31) , 10653-10656. https://doi.org/10.1021/jacs.7b06340
  40. Yun-Bing Zhou, Yu-Qing Wang, Li-Chao Ning, Zong-Cang Ding, Wen-Long Wang, Cheng-Ke Ding, Ren-Hao Li, Jun-Jia Chen, Xin Lu, Yun-Jie Ding, and Zhuang-Ping Zhan . Conjugated Microporous Polymer as Heterogeneous Ligand for Highly Selective Oxidative Heck Reaction. Journal of the American Chemical Society 2017, 139 (11) , 3966-3969. https://doi.org/10.1021/jacs.7b00643
  41. Jillian S. K. Clark, Christopher N. Voth, Michael J. Ferguson, and Mark Stradiotto . Evaluating 1,1′-Bis(phosphino)ferrocene Ancillary Ligand Variants in the Nickel-Catalyzed C–N Cross-Coupling of (Hetero)aryl Chlorides. Organometallics 2017, 36 (3) , 679-686. https://doi.org/10.1021/acs.organomet.6b00885
  42. Shin Ando, Hirofumi Matsunaga, and Tadao Ishizuka . An N-Heterocyclic Carbene-Nickel Half-Sandwich Complex as a Precatalyst for Suzuki–Miyaura Coupling of Aryl/Heteroaryl Halides with Aryl/Heteroarylboronic Acids. The Journal of Organic Chemistry 2017, 82 (2) , 1266-1272. https://doi.org/10.1021/acs.joc.6b02666
  43. Megan Mohadjer Beromi, Ainara Nova, David Balcells, Ann M. Brasacchio, Gary W. Brudvig, Louise M. Guard, Nilay Hazari, and David J. Vinyard . Mechanistic Study of an Improved Ni Precatalyst for Suzuki–Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species. Journal of the American Chemical Society 2017, 139 (2) , 922-936. https://doi.org/10.1021/jacs.6b11412
  44. Vitor H. Menezes da Silva, Ataualpa A. C. Braga, and Thomas R. Cundari . N-Heterocyclic Carbene Based Nickel and Palladium Complexes: A DFT Comparison of the Mizoroki–Heck Catalytic Cycles. Organometallics 2016, 35 (18) , 3170-3181. https://doi.org/10.1021/acs.organomet.6b00532
  45. Jillian S. K. Clark, Christopher M. Lavoie, Preston M. MacQueen, Michael J. Ferguson, and Mark Stradiotto . A Comparative Reactivity Survey of Some Prominent Bisphosphine Nickel(II) Precatalysts in C–N Cross-Coupling. Organometallics 2016, 35 (18) , 3248-3254. https://doi.org/10.1021/acs.organomet.6b00650
  46. Jacob E. Dander, Nicholas A. Weires, and Neil K. Garg . Benchtop Delivery of Ni(cod)2 using Paraffin Capsules. Organic Letters 2016, 18 (15) , 3934-3936. https://doi.org/10.1021/acs.orglett.6b01758
  47. Andrew J. Hoover, Mark Lazari, Hong Ren, Maruthi Kumar Narayanam, Jennifer M. Murphy, R. Michael van Dam, Jacob M. Hooker, and Tobias Ritter . A Transmetalation Reaction Enables the Synthesis of [18F]5-Fluorouracil from [18F]Fluoride for Human PET Imaging. Organometallics 2016, 35 (7) , 1008-1014. https://doi.org/10.1021/acs.organomet.6b00059
  48. Chi Yang, Wen-Di Wu, Liang Zhao, and Mei-Xiang Wang . Macrocyclic Aryl–Nickel(II) Complexes: Synthesis, Structure, and Reactivity Studies. Organometallics 2015, 34 (20) , 5167-5174. https://doi.org/10.1021/acs.organomet.5b00733
  49. Xin Hong, Jinglin Wang, Yun-Fang Yang, Lisi He, Chun-Yu Ho, and K. N. Houk . Computational Exploration of Mechanism and Selectivities of (NHC)Nickel(II)hydride-Catalyzed Hydroalkenylations of Styrene with α-Olefins. ACS Catalysis 2015, 5 (9) , 5545-5555. https://doi.org/10.1021/acscatal.5b01075
  50. Alex J. Nett, Wanxiang Zhao, Paul M. Zimmerman, and John Montgomery . Highly Active Nickel Catalysts for C–H Functionalization Identified through Analysis of Off-Cycle Intermediates. Journal of the American Chemical Society 2015, 137 (24) , 7636-7639. https://doi.org/10.1021/jacs.5b04548
  51. Mohammad Hassam, Abu Taher, Gareth E. Arnott, Ivan R. Green, and Willem A. L. van Otterlo . Isomerization of Allylbenzenes. Chemical Reviews 2015, 115 (11) , 5462-5569. https://doi.org/10.1021/acs.chemrev.5b00052
  52. Eric A. Standley, Sarah Z. Tasker, Kim L. Jensen, and Timothy F. Jamison . Nickel Catalysis: Synergy between Method Development and Total Synthesis. Accounts of Chemical Research 2015, 48 (5) , 1503-1514. https://doi.org/10.1021/acs.accounts.5b00064
  53. Jason D. Shields, Erin E. Gray, and Abigail G. Doyle . A Modular, Air-Stable Nickel Precatalyst. Organic Letters 2015, 17 (9) , 2166-2169. https://doi.org/10.1021/acs.orglett.5b00766
  54. Javier Magano and Sebastien Monfette . Development of an Air-Stable, Broadly Applicable Nickel Source for Nickel-Catalyzed Cross-Coupling. ACS Catalysis 2015, 5 (5) , 3120-3123. https://doi.org/10.1021/acscatal.5b00498
  55. Ryan L. Jezorek, Na Zhang, Pawaret Leowanawat, Matthew H. Bunner, Nicholas Gutsche, Aleksander K. R. Pesti, James T. Olsen, and Virgil Percec . Air-Stable Nickel Precatalysts for Fast and Quantitative Cross-Coupling of Aryl Sulfamates with Aryl Neopentylglycolboronates at Room Temperature. Organic Letters 2014, 16 (24) , 6326-6329. https://doi.org/10.1021/ol503061c
  56. Kim L. Jensen, Eric A. Standley, and Timothy F. Jamison . Highly Regioselective Nickel-Catalyzed Cross-Coupling of N-Tosylaziridines and Alkylzinc Reagents. Journal of the American Chemical Society 2014, 136 (31) , 11145-11152. https://doi.org/10.1021/ja505823s
  57. Michael R. Harris, Mikhail O. Konev, and Elizabeth R. Jarvo . Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers. Journal of the American Chemical Society 2014, 136 (22) , 7825-7828. https://doi.org/10.1021/ja5026485
  58. Alec H. Christian, Peter Müller, and Sebastien Monfette . Nickel Hydroxo Complexes as Intermediates in Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling. Organometallics 2014, 33 (9) , 2134-2137. https://doi.org/10.1021/om5001327
  59. Eric A. Standley, Stacey J. Smith, Peter Müller, and Timothy F. Jamison . A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes. Organometallics 2014, 33 (8) , 2012-2018. https://doi.org/10.1021/om500156q
  60. Jason D. Shields, Derek T. Ahneman, Thomas J. A. Graham, and Abigail G. Doyle . Enantioselective, Nickel-Catalyzed Suzuki Cross-Coupling of Quinolinium Ions. Organic Letters 2014, 16 (1) , 142-145. https://doi.org/10.1021/ol4031364
  61. Nathaniel H. Park, Georgiy Teverovskiy, and Stephen L. Buchwald . Development of an Air-Stable Nickel Precatalyst for the Amination of Aryl Chlorides, Sulfamates, Mesylates, and Triflates. Organic Letters 2014, 16 (1) , 220-223. https://doi.org/10.1021/ol403209k
  62. Sandeep Kumar Thakur, Mandeep Kaur, Krishna Kumar Manar, Manu Adhikari, Angshuman Roy Choudhury, Sanjay Singh. Well‐Defined Ni(0) and Ni(II) Complexes of Bicyclic (Alkyl)(Amino)Carbene ( Me BICAAC): Catalytic Activity and Mechanistic Insights in Negishi Cross‐Coupling Reaction. Chemistry – A European Journal 2022, https://doi.org/10.1002/chem.202202237
  63. Sai Manoj N. V. T. Gorantla, Kartik Chandra Mondal. The Labile Nature of Air Stable Ni(II)/Ni(0)‐phosphine/Olefin Catalysts/Intermediates: EDA‐NOCV Analysis. Chemistry – An Asian Journal 2022, 60 https://doi.org/10.1002/asia.202200572
  64. Kun Liu, Dirk Leifert, Armido Studer. Cooperative triple catalysis enables regioirregular formal Mizoroki–Heck reactions. Nature Synthesis 2022, 1 (7) , 565-575. https://doi.org/10.1038/s44160-022-00101-9
  65. Yunlong Zhao, Chen‐Fei Liu, Leroy Qi Hao Lin, Albert S. C. Chan, Ming Joo Koh. Stereoselective Synthesis of Trisubstituted Alkenes by Nickel‐Catalyzed Benzylation and Alkene Isomerization. Angewandte Chemie 2022, 134 (26) https://doi.org/10.1002/ange.202202674
  66. Yunlong Zhao, Chen‐Fei Liu, Leroy Qi Hao Lin, Albert S. C. Chan, Ming Joo Koh. Stereoselective Synthesis of Trisubstituted Alkenes by Nickel‐Catalyzed Benzylation and Alkene Isomerization. Angewandte Chemie International Edition 2022, 61 (26) https://doi.org/10.1002/anie.202202674
  67. Ryan T. McGuire, Travis Lundrigan, Joshua W. M. MacMillan, Katherine N. Robertson, Arun A. Yadav, Mark Stradiotto. Mapping Dual‐Base‐Enabled Nickel‐Catalyzed Aryl Amidations: Application in the Synthesis of 4‐Quinolones. Angewandte Chemie 2022, https://doi.org/10.1002/ange.202200352
  68. Ryan T. McGuire, Travis Lundrigan, Joshua W. M. MacMillan, Katherine N. Robertson, Arun A. Yadav, Mark Stradiotto. Mapping Dual‐Base‐Enabled Nickel‐Catalyzed Aryl Amidations: Application in the Synthesis of 4‐Quinolones. Angewandte Chemie International Edition 2022, https://doi.org/10.1002/anie.202200352
  69. Shenghan Teng, Jianrong Steve Zhou. C C Bond Formation Through Heck-Like Reactions. 2022,,, 2-45. https://doi.org/10.1016/B978-0-12-820206-7.00156-6
  70. Clifton L. Wagner, Tianning Diao. Nickel-Carbon σ-Bonded Complexes. 2022,,, 271-356. https://doi.org/10.1016/B978-0-12-820206-7.00141-4
  71. Yunlong Li, Haibo Liu, Zilong Huang, Hongmei Wang, Zhengkun Yu. Palladium-catalyzed cross-dehydrogenative-coupling of nitro-substituted internal alkenes with terminal alkenes. Tetrahedron Letters 2021, 82 , 153396. https://doi.org/10.1016/j.tetlet.2021.153396
  72. Xian Zhao, Shengqing Zhu, Feng-Ling Qing, Lingling Chu. Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis. Chemical Communications 2021, 57 (74) , 9414-9417. https://doi.org/10.1039/D1CC03668H
  73. Chen-Fei Liu, Hongyu Wang, Robert T. Martin, Haonan Zhao, Osvaldo Gutierrez, Ming Joo Koh. Olefin functionalization/isomerization enables stereoselective alkene synthesis. Nature Catalysis 2021, 4 (8) , 674-683. https://doi.org/10.1038/s41929-021-00658-2
  74. S. Bhakta, T. Ghosh. Emerging Nickel Catalysis in Heck Reactions: Recent Developments. Advanced Synthesis & Catalysis 2020, 362 (23) , 5257-5274. https://doi.org/10.1002/adsc.202000820
  75. Qiao Li, Yun Cai, Hongwei Jin, Yunkui Liu, Bingwei Zhou. Nickel-catalyzed aminocarbonylation of Aryl/Alkenyl/Allyl (pseudo)halides with isocyanides and H2O. Tetrahedron Letters 2020, 61 (51) , 152605. https://doi.org/10.1016/j.tetlet.2020.152605
  76. Schirin Hanf, Toni Grell, Jessica E. Waters, Raúl García-Rodríguez, Evamarie Hey-Hawkins, Dominic S. Wright. Facile synthesis of a nickel(0) phosphine complex at ambient temperature. Chemical Communications 2020, 56 (57) , 7893-7896. https://doi.org/10.1039/D0CC02142C
  77. Yuchen He., Zhicong Tang, Gang Hong, Chen Hu, Chen Zhou, Limin Wang. Scandium(III) Trifluoromethanesulfonate Catalyzed Reactions of 9‐Aryl‐9‐fluorenols with 1,1‐Diarylethylenes. ChemistrySelect 2020, 5 (20) , 6178-6181. https://doi.org/10.1002/slct.202000814
  78. Van T. Tran, Zi‐Qi Li, Omar Apolinar, Joseph Derosa, Matthew V. Joannou, Steven R. Wisniewski, Martin D. Eastgate, Keary M. Engle. Ni(COD)(DQ): An Air‐Stable 18‐Electron Nickel(0)–Olefin Precatalyst. Angewandte Chemie 2020, 132 (19) , 7479-7483. https://doi.org/10.1002/ange.202000124
  79. Van T. Tran, Zi‐Qi Li, Omar Apolinar, Joseph Derosa, Matthew V. Joannou, Steven R. Wisniewski, Martin D. Eastgate, Keary M. Engle. Ni(COD)(DQ): An Air‐Stable 18‐Electron Nickel(0)–Olefin Precatalyst. Angewandte Chemie International Edition 2020, 59 (19) , 7409-7413. https://doi.org/10.1002/anie.202000124
  80. Lukas Nattmann, Rakan Saeb, Nils Nöthling, Josep Cornella. An air-stable binary Ni(0)–olefin catalyst. Nature Catalysis 2020, 3 (1) , 6-13. https://doi.org/10.1038/s41929-019-0392-6
  81. Timothy B. Boit, Katie A. Spence, Neil K. Garg. From glovebox to benchtop. Nature Catalysis 2020, 3 (1) , 2-3. https://doi.org/10.1038/s41929-019-0407-3
  82. Tetsuya Tsujihara, Moriho Tomeba, Shigeaki Ohkubo-Sato, Kyoko Iwabuchi, Rino Koie, Natsumi Tada, Satoru Tamura, Tsunayoshi Takehara, Takeyuki Suzuki, Tomikazu Kawano. One-pot reactions of bicyclic zinc enolate generated from Ni-catalyzed reductive cyclization to furnish octahydro-4,7-ethanobenzofuran-9-one derivatives. Tetrahedron Letters 2019, 60 (42) , 151148. https://doi.org/10.1016/j.tetlet.2019.151148
  83. Mikhail V. Polynski, Evgeny A. Pidko. Intermetallic species in the Negishi coupling and their involvement in inhibition pathways. Catalysis Science & Technology 2019, 9 (17) , 4561-4572. https://doi.org/10.1039/C9CY00752K
  84. Satyendra Mishra, Chandni G Halpani, Sejal Patel. Nickel‐Catalyzed Heck Reaction of Aryl Halides and Terminal Olefins Using Zinc/Triflate Ligand/DMA/TBAB. ChemistrySelect 2019, 4 (23) , 6913-6916. https://doi.org/10.1002/slct.201901131
  85. Li Chen, Yoshio Hisaeda, Hisashi Shimakoshi. Visible Light‐Driven, Room Temperature Heck‐Type Reaction of Alkyl Halides with Styrene Derivatives Catalyzed by B 12 Complex. Advanced Synthesis & Catalysis 2019, 361 (12) , 2877-2884. https://doi.org/10.1002/adsc.201801707
  86. Shaoke Zhang, Nicolas Rotta-Loria, Florian Weniger, Jabor Rabeah, Helfried Neumann, Christoph Taeschler, Matthias Beller. A general and practical Ni-catalyzed C–H perfluoroalkylation of (hetero)arenes. Chemical Communications 2019, 55 (47) , 6723-6726. https://doi.org/10.1039/C9CC01971E
  87. Angelo Frei. Synthetic Routes towards Multifunctional Cyclopentadienes. Chemistry – A European Journal 2019, 25 (29) , 7074-7090. https://doi.org/10.1002/chem.201900276
  88. Yi Yang, Qinghai Zhou, Junjie Cai, Teng Xue, Yingle Liu, Yan Jiang, Yumei Su, Lungwa Chung, David A. Vicic. Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations. Chemical Science 2019, 10 (20) , 5275-5282. https://doi.org/10.1039/C9SC00554D
  89. Wen-Hao Li, Cun-Yao Li, Huan-Yan Xiong, Yang Liu, Wen-Yong Huang, Guang-Jun Ji, Zheng Jiang, Hai-Tao Tang, Ying-Ming Pan, Yun-Jie Ding. Constructing Mononuclear Palladium Catalysts by Precoordination/Solvothermal Polymerization: Recyclable Catalyst for Regioselective Oxidative Heck Reactions. Angewandte Chemie 2019, 131 (8) , 2470-2475. https://doi.org/10.1002/ange.201814493
  90. Wen‐Hao Li, Cun‐Yao Li, Huan‐Yan Xiong, Yang Liu, Wen‐Yong Huang, Guang‐Jun Ji, Zheng Jiang, Hai‐Tao Tang, Ying‐Ming Pan, Yun‐Jie Ding. Constructing Mononuclear Palladium Catalysts by Precoordination/Solvothermal Polymerization: Recyclable Catalyst for Regioselective Oxidative Heck Reactions. Angewandte Chemie International Edition 2019, 58 (8) , 2448-2453. https://doi.org/10.1002/anie.201814493
  91. Yohei Ueda, Nagataka Tsujimoto, Taiga Yurino, Hayato Tsurugi, Kazushi Mashima. Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile via C–CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine. Chemical Science 2019, 10 (4) , 994-999. https://doi.org/10.1039/C8SC04437F
  92. Chao Ren, Jingshu Zeng, Gang Zou. Nickel-catalyzed cross-coupling of O , N -chelated diarylborinates with aryl chlorides and mesylates. New Journal of Chemistry 2019, 43 (3) , 1589-1596. https://doi.org/10.1039/C8NJ05503C
  93. Megan R. Kwiatkowski, Erik J. Alexanian. Nickel‐Catalyzed Mizoroki–Heck‐Type Reactions of Unactivated Alkyl Bromides. Angewandte Chemie 2018, 130 (51) , 17099-17102. https://doi.org/10.1002/ange.201810757
  94. Megan R. Kwiatkowski, Erik J. Alexanian. Nickel‐Catalyzed Mizoroki–Heck‐Type Reactions of Unactivated Alkyl Bromides. Angewandte Chemie International Edition 2018, 57 (51) , 16857-16860. https://doi.org/10.1002/anie.201810757
  95. Ran Ding, Borong Yu. Palladium‐Catalyzed Direct Methylation and Benzylation of Enamides Using Iodomethane and Benzyl Halides with Retention of Alkenyl Moiety. Asian Journal of Organic Chemistry 2018, 7 (12) , 2427-2430. https://doi.org/10.1002/ajoc.201800535
  96. Joseph B. Sweeney, Anthony K. Ball, Philippa A. Lawrence, Mackenzie C. Sinclair, Luke J. Smith. A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols. Angewandte Chemie 2018, 130 (32) , 10359-10363. https://doi.org/10.1002/ange.201805611
  97. Joseph B. Sweeney, Anthony K. Ball, Philippa A. Lawrence, Mackenzie C. Sinclair, Luke J. Smith. A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols. Angewandte Chemie International Edition 2018, 57 (32) , 10202-10206. https://doi.org/10.1002/anie.201805611
  98. Felix Strieth-Kalthoff, Ashley R. Longstreet, Jessica M. Weber, Timothy F. Jamison. Bench-Stable N -Heterocyclic Carbene Nickel Precatalysts for C−C and C−N Bond-Forming Reactions. ChemCatChem 2018, 10 (13) , 2873-2877. https://doi.org/10.1002/cctc.201800454
  99. Jianchen Shen, Biping Xu, Min Zhang, Weiping Su. Branched-Selective Decarboxylative Heck Reaction with Electronically Unbiased Olefins. European Journal of Organic Chemistry 2018, 2018 (22) , 2768-2773. https://doi.org/10.1002/ejoc.201800330
  100. Joseph B. Sweeney, Anthony K. Ball, Luke J. Smith. Catalytic C−C Bond Formation Using a Simple Nickel Precatalyst System: Base‐ and Activator‐Free Direct C‐Allylation by Alcohols and Amines. Chemistry – A European Journal 2018, 24 (29) , 7354-7357. https://doi.org/10.1002/chem.201801241
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