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

页码：6375 / 6381

页数：7

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