Cobalt-Catalyzed Addition of Arylzinc Reagents to Alkynes to Form ortho-Alkenylarylzinc Species through 1,4-Cobalt Migration

被引：103

作者：

Tan, Boon-Hong ^{[1
]}

Dong, Jinghua ^{[1
]}

Yoshikai, Naohiko ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 38期

基金：

新加坡国家研究基金会;

关键词：

alkynes; C-H activation; cobalt; multicomponent couplings; organozinc reagents; C-H BOND; PALLADIUM MIGRATION; RHODIUM; ACTIVATION; IRON; ARYLMAGNESIATION; HYDROARYLATION; SUBSTITUENTS; DERIVATIVES; INSERTION;

D O I：

10.1002/anie.201204388

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Migratory carbometalation: A cobalt-Xantphos complex catalyzes the addition of an arylzinc reagent to an unactivated internal alkyne; the reaction most likely involves insertion of the alkyne into an arylcobalt species and vinyl-to-aryl 1,4-cobalt migration, followed by transmetalation with the arylzinc reagent. Interception of the resulting ortho-alkenylarylzinc species with electrophiles allows access to 1-alkenyl arenes functionalized in the 2-position. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9610 / 9614

页数：5

共 4 条

[1] Cobalt-Catalyzed Addition of Arylzinc Reagents to Norbornene Derivatives through 1,4-Cobalt Migration
Tan, Boon-Hong
Yoshikai, Naohiko
ORGANIC LETTERS, 2014, 16 (12) : 3392 - 3395
[2] Cobalt-Catalyzed Arylative Cyclization of Acetylenic Esters and Ketones with Arylzinc Reagents through 1,4-Cobalt Migration
Yan, Jianming
Yoshikai, Naohiko
ACS CATALYSIS, 2016, 6 (06): : 3738 - 3742
[3] Functionalization of the Benzylic C-H Bonds in Azaarenes by Cobalt-Catalyzed 1,4-Addition to Enones
Jamal, Zaini
Teo, Yong-Chua
Wong, Ling-Keong
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (33) : 7343 - 7346
[4] Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides
Gillaizeau-Simonian, Nicolas
Barde, Etienne
Guerinot, Amandine
Cossy, Janine
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (12) : 4004 - 4008

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