A Redox Transmetalation Step in Nickel-Catalyzed C-C Coupling Reactions

被引：7
|
作者：
Green, Kerry-Ann [1 ,2 ]
Honeycutt, Aaron P. [1 ]
Ciccone, Sierra R. [1 ]
Grice, Kyle A. [1 ,3 ]
Baur, Andreas [1 ]
Petersen, Jeffrey L. [1 ]
Hoover, Jessica M. [1 ]
机构：
[1] West Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA
[2] Williams Coll, Dept Chem, Williamstown, MA 01267 USA
[3] DePaul Univ, Dept Chem & Biochem, Chicago, IL 60614 USA
来源：
ACS CATALYSIS | 2023年 / 13卷 / 09期
关键词：
nickel; silver; cross-coupling; transmetalation; reductive elimination; metallacycle; redox; HYPERVALENT IODINE(III) REAGENTS; FORMING REDUCTIVE ELIMINATION; H BONDS; 4-TETRAFLUOROPYRIDYL SILVER(I); DECARBONYLATIVE ADDITION; DIORGANOZINC REAGENTS; SYNTHETIC CHEMISTRY; SELECTIVE FORMATION; CARBONYL-COMPLEXES; CRYSTAL-STRUCTURE;
D O I：
10.1021/acscatal.2c06015
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Ni-catalyzed C-H functionalization reactions are becoming efficient routes to access a variety of functionalized arenes, yet the mechanisms of these catalytic C-C coupling reactions are not well understood. Here, we report the catalytic and stoichiometric arylation reactions of a nickel(II) metallacycle. Treatment of this species with silver(I)-aryl complexes results in facile arylation, consistent with a redox transmetalation step. Additionally, treatment with electrophilic coupling partners generates C-C and C-S bonds. We anticipate that this redox transmetalation step may be relevant to other coupling reactions that employ silver salts as additives.
引用
收藏
页码：6375 / 6381
页数：7
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