Ligand-free nickel-catalyzed Kumada couplings of aryl bromides with tert-butyl Grignard reagents
-
* Corresponding authors.
E-mail addresses: xubin@shu.edu.cn (B. Xu), tangwenjun@sioc.ac.cn (W. Tang)
Citation: Wu Zhenghan, Si Tengda, Xu Guangqing, Xu Bin, Tang Wenjun. Ligand-free nickel-catalyzed Kumada couplings of aryl bromides with tert-butyl Grignard reagents[J]. Chinese Chemical Letters, ;2019, 30(3): 597-600. doi: 10.1016/j.cclet.2018.12.027
(a) A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, New York, 2004;
(b) M. Beller, C. Bolm (Eds.), Transition Metals for Organic Synthesis, Wiley-VCH, Weinheim, 2004;
(c) A. Rudolph, M. Lautens, Angew. Chem. Int. Ed. 48 (2009) 2656-2670.
(a) T.W. Bell, L. Hu, S.V. Patelf, J. Org. Chem. 52 (1987) 3847-3850;
(b) S.R. Chemler, D. Trauner, S.J. Danishefsky, Angew. Chem. Int. Ed. 40 (2001) 4544-4568;
(c) M.R. Netherton, G.C. Fu, in: J. Tsuji (Ed.), Topics in Organometallic Chemistry: Palladium in Organic Synthesis, Springer, New York, 2005, pp. 85-108;
(d) S.L. Zultanski, G.C. Fu, J. Am. Chem. Soc. 135 (2013) 624-627;
(e) X. Wang, S. Wang, W. Xue, H. Gong, J. Am. Chem. Soc. 137 (2015) 11562-11565;
(f) S. Ando, M. Mawatari, H. Matsunaga, T. Ishizuka, Tetrahedron Lett. 57 (2016) 3287-3290;
(g) G. Wang, R. Shang, W. Cheng, Y. Fu, J. Am. Chem. Soc. 139 (2017) 18307-18312;
(h) D.N. Primer, G.A. Molander, J. Am. Chem. Soc. 139 (2017) 9847-9850;
(i) Z.T. Ariki, Y. Maekawa, M. Nambo, C.M. Crudden, J. Am. Chem. Soc. 140 (2018) 78-81.
(a) C. Li, T. Chen, W. Tang, Angew. Chem. Int. Ed. 54 (2015) 3792-3796;
(b) T. Si, B. Li, W. Xiong, B. Xu, W. Tang, Org. Biomol. Chem.15 (2017) 9903-9909.
(a) X. Luo, H. Zhang, H. Duan, et al., Org. Lett. 9 (2007) 4571-4574;
(b) J. Breitenfeld, O. Vechorkin, C. Corminboeuf, R. Scopelliti, X. Hu, Organometallics 29 (2010) 3686-3689.
T. Hayashi, M. Konishi, K. Yokota, M. Kumada, Chem. Lett. 9 (1980) 767-768.
doi: 10.1246/cl.1980.767
A. Joshi-Pangu, C. Wang, M.R. Biscoe, J. Am. Chem. Soc. 133 (2011) 8478-8481.
doi: 10.1021/ja202769t
C. Lohre, T. Dröge, C. Wang, F. Glorius, Chem.-Eur. J. 17 (2011) 6052-6055.
doi: 10.1002/chem.v17.22
(a) T.J. Anderson, G.D. Jones, D.A. Vicic, J. Am. Chem. Soc. 126 (2004) 8100-8101;
(b) G.D. Jones, J.L. Martin, C. McFarland, et al., J. Am. Chem. Soc. 128 (2006) 13175-13183;
(c) V.B. Phapale, M. Guisán-Ceinos, E. Buñuel, D.J. Cárdenas, Chem.-Eur. J. 15 (2009) 12681-12688;
(d) K. Zhang, M.C. Sheridan, S.R. Cooke, J. Louie, Organometallics 30 (2011) 2546-2552;
(e) F. Han, Chem. Soc. Rev. 42 (2013) 5270-5298;
(f) S. Biswas, D.J. Weix, J. Am. Chem. Soc. 135 (2013) 16192-16197;
(g) K.C. Shekhar, R.K. Dhungana, B. Shrestha, et al., J. Am. Chem. Soc. 140 (2018) 9801-9805.
Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
Yuhan Liu , Jingyang Zhang , Gongming Yang , Jian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790
Jumei Zhang , Ziheng Zhang , Gang Li , Hongjin Qiao , Hua Xie , Ling Jiang . Ligand-mediated reactivity in CO oxidation of yttrium-nickel monoxide carbonyl complexes. Chinese Chemical Letters, 2025, 36(2): 110278-. doi: 10.1016/j.cclet.2024.110278
Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp3)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO3−x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
Xiao-Bo Liu , Ren-Ming Liu , Xiao-Di Bao , Hua-Jian Xu , Qi Zhang , Yu-Feng Liang . Nickel-catalyzed reductive formylation of aryl halides via formyl radical. Chinese Chemical Letters, 2024, 35(12): 109783-. doi: 10.1016/j.cclet.2024.109783
Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
Luyao Lu , Chen Zhu , Fei Li , Pu Wang , Xi Kang , Yong Pei , Manzhou Zhu . Ligand effects on geometric structures and catalytic activities of atomically precise copper nanoclusters. Chinese Journal of Structural Chemistry, 2024, 43(10): 100411-100411. doi: 10.1016/j.cjsc.2024.100411
Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372