Nickel-Catalyzed C(sp3)-C(sp3) Cross-Electrophile Coupling of InSitu Generated NHP Esters with Unactivated Alkyl Bromides

被引:36
作者
Kang, Kai [1 ]
Weix, Daniel J. [1 ]
机构
[1] Univ Wisconsin, Madison, WI 53706 USA
关键词
REDOX-ACTIVE ESTERS; HALIDES; OXIDATION; DECARBOXYLATION; NI;
D O I
10.1021/acs.orglett.2c00805
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The formation of C(sp3)-C(sp3) bonds by cross-coupling remains a challenge in synthesis. Here, we demonstrate atwo-step, one-pot protocol for the in situ generation ofN-hydroxyphthalimide esters and their nickel-catalyzed cross-electrophilecoupling with unactivated alkyl bromides for the construction of 1 degrees/1 degrees C(sp3)-C(sp3) bonds. The conditions tolerate an array of functionalgroups, and mechanistic studies indicate that both substrates areconverted to alkyl radicals during the reaction.
引用
收藏
页码:2853 / 2857
页数:5
相关论文
共 69 条
[11]   Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters [J].
Cornella, Josep ;
Edwards, Jacob T. ;
Qin, Tian ;
Kawamura, Shuhei ;
Wang, Jie ;
Pan, Chung-Mao ;
Gianatassio, Ryan ;
Schmidt, Michael ;
Eastgate, Martin D. ;
Baran, Phil S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (07) :2174-2177
[12]   Transition-Metal Catalysis of Nucleophilic Substitution Reactions: A Radical Alternative to SN1 and SN2 Processes [J].
Fu, Gregory C. .
ACS CENTRAL SCIENCE, 2017, 3 (07) :692-700
[13]   sp3-sp3 Coupling reactions in the synthesis of natural products and biologically active molecules [J].
Geist, Egor ;
Kirschning, Andreas ;
Schmidt, Thomas .
NATURAL PRODUCT REPORTS, 2014, 31 (04) :441-448
[14]  
Goldfogel MJ, 2020, NICKEL CATALYSIS IN ORGANIC SYNTHESIS: METHODS AND REACTIONS, P183
[15]   Hydroalkylation of Olefins To Form Quaternary Carbons [J].
Green, Samantha A. ;
Huffman, Tucker R. ;
McCourt, Ruairi O. ;
van der Puyl, Vincent ;
Shenvi, Ryan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (19) :7709-7714
[16]   Nickel-catalyzed reductive coupling of alkyl halides with other electrophiles: concept and mechanistic considerations [J].
Gu, Jun ;
Wang, Xuan ;
Xue, Weichao ;
Gong, Hegui .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10) :1411-1421
[17]   Modular terpene synthesis enabled by mild electrochemical couplings [J].
Harwood, Stephen J. ;
Palkowitz, Maximilian D. ;
Gannett, Cara N. ;
Perez, Paulo ;
Yao, Zhen ;
Sun, Lijie ;
Abruna, Hector D. ;
Anderson, Scott L. ;
Baran, Phil S. .
SCIENCE, 2022, 375 (6582) :745-+
[18]   Chemoselective and fast decarboxylative allylation by photoredox catalysis under mild conditions [J].
Hu, Chenchen ;
Chen, Yiyun .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10) :1352-1355
[19]   Nickel-catalyzed cross coupling of non-activated alkyl halides: a mechanistic perspective [J].
Hu, Xile .
CHEMICAL SCIENCE, 2011, 2 (10) :1867-1886
[20]   Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners [J].
Jana, Ranjan ;
Pathak, Tejas P. ;
Sigman, Matthew S. .
CHEMICAL REVIEWS, 2011, 111 (03) :1417-1492