Carboxyzincation Employing Carbon Dioxide and Zinc Powder: Cobalt-Catalyzed Multicomponent Coupling Reactions with Alkynes

被引：96

作者：

Nogi, Keisuke ^{[1
]}

Fujihara, Tetsuaki ^{[1
]}

Terao, Jun ^{[1
]}

Tsuji, Yasushi ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Nishikyo Ku, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 17期

关键词：

OXANICKELACYCLOPENTENE DERIVATIVES; CARBOXYLATIVE CYCLIZATION; ALKYLATIVE CARBOXYLATION; FUNCTIONALIZED ARYLZINC; REDUCTIVE CARBOXYLATION; UNACTIVATED PRIMARY; ACTIVATED ALKENES; ORGANIC-SYNTHESIS; BENZYL HALIDES; CO2;

D O I：

10.1021/jacs.6b02961

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cobalt-catalyzed carboxyzincation reactions employing carbon dioxide and zinc metal powder are developed. By using alkynes as substrates, regio- and stereodefined (Z)-beta-zincated acrylates are provided. The corresponding alkenylzinc moiety can be converted to various substituents, affording multisubstituted acrylic acids. Furthermore, by adding electron-deficient alkene to the reaction system, the four-component coupling reactions of alkyne, alkene, CO2, and the Zn atom proceed via carboxyzincation.

引用

页码：5547 / 5550

页数：4

共 54 条

[1]

[Anonymous], COMPREHENSIVE ORGANI

[2]

Aresta M., 1969, INORG CHIM ACTA, V3, P227, DOI 10.1016/S0020-1693(00)92484-8

[3] OXANICKELACYCLOPENTENE DERIVATIVES FROM NICKEL(0), CARBON-DIOXIDE, AND ALKYNES [J].

BURKHART, G ;

HOBERG, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (01) :76-76

[4] Cobalt-catalyzed reductive coupling of activated alkenes with alkynes [J].

Chang, Hong-Tai ;

Jayanth, Thiruvellore Thatai ;

Wang, Chun-Chih ;

Cheng, Chien-Hong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :12032-12041

[5] Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes [J].

Cheung, Chi Wai ;

Zhurkin, Fedor E. ;

Hu, Xile .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) :4932-4935

[6] Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge? [J].

Cokoja, Mirza ;

Bruckmeier, Christian ;

Rieger, Bernhard ;

Herrmann, Wolfgang A. ;

Kuehn, Fritz E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8510-8537

[7] Ni-Catalyzed Carboxylation of C(sp2)- and C(sp3)-O Bonds with CO2 [J].

Correa, Arkaitz ;

Leon, Thierry ;

Martin, Ruben .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :1062-1069

[8] Metal mediated carbometallation of alkynes and alkenes containing adjacent heteroatoms [J].

Fallis, AG ;

Forgione, P .

TETRAHEDRON, 2001, 57 (28) :5899-5913

[9] New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust [J].

Fillon, H ;

Gosmini, C ;

Périchon, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3867-3870

[10] Stereocontrolled synthesis of tetrasubstituted olefins [J].

Flynn, Alison B. ;

Ogilvie, William W. .

CHEMICAL REVIEWS, 2007, 107 (11) :4698-4745

← 1 2 3 4 5 6 →