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

共 50 条

[1] Nickel-Catalyzed Highly Atom-Economical C-C Coupling Reactions with Components
Xiao, Li-Jun
Ye, Meng-Chun
Zhou, Qi-Lin
SYNLETT, 2019, 30 (04) : 361 - 369
[2] Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles
Russell, John E. A.
Entz, Emily D.
Joyce, Ian M.
Neufeldt, Sharon R.
ACS CATALYSIS, 2019, 9 (04): : 3304 - 3310
[3] Nickel-catalyzed coupling reactions of alkenes
Ng, Sze-Sze
Ho, Chun-Yu
Schleicher, Kristin D.
Jamison, Timothy F.
PURE AND APPLIED CHEMISTRY, 2008, 80 (05) : 929 - 939
[4] Nickel-catalyzed dual C-C σ bond activation to construct carbocyclic skeletons
Nakai, Kenichiro
Kurahashi, Takuya
Matsubara, Seijiro
TETRAHEDRON, 2015, 71 (26-27) : 4512 - 4517
[5] Nickel-catalyzed C(sp2)-C(sp2) Cross Coupling Reactions of Sulfur-Functionalities and Grignard Reagents
Someya, Chika I.
Weidauer, Maik
Enthaler, Stephan
CATALYSIS LETTERS, 2013, 143 (05) : 424 - 431
[6] Advances in Gold-Catalyzed C-C Coupling Reactions
Zhang, Yan
Luo, Sha
Zhu, Chengjian
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (11) : 2073 - 2080
[7] Nickel-Catalyzed Cross-Coupling of Aryl Pivalates with Cyclobutanols Involving C-O and C-C Bond Cleavage
Gan, Yi
Zhang, Ninghui
Huang, Shaoxu
Liu, Yuanhong
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1686 - 1690
[8] Taming Nickel-Catalyzed Suzuki-Miyaura Coupling: A Mechanistic Focus on Boron-to-Nickel Transmetalation
Payard, Pierre-Adrien
Perego, Luca Alessandro
Ciofini, Ilaria
Grimaud, Laurence
ACS CATALYSIS, 2018, 8 (06): : 4812 - 4823
[9] Photoinduced nickel-catalyzed enantioselective coupling reactions
Li, Zhilong
Li, Chengyang
Ding, Yu
Huo, Haohua
COORDINATION CHEMISTRY REVIEWS, 2022, 460
[10] Nickel-Catalyzed C-P Cross-Coupling by C-CN Bond Cleavage
Sun, Meng
Zhang, Hong-Yu
Han, Qi
Yang, Kuo
Yang, Shang-Dong
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (35) : 9566 - 9570

← 1 2 3 4 5 →