Cobalt-Catalyzed Reductive Carboxylation of α,β-Unsaturated Compounds with Carbon Dioxide

被引：21

作者：

Hayashi, Chika ^{[1
]}

Hayashi, Takuo ^{[1
]}

Yamada, Tohru ^{[1
]}

机构：

[1] Keio Univ, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2015年 / 88卷 / 06期

关键词：

ENANTIOSELECTIVE BOROHYDRIDE REDUCTION; ASYMMETRIC ALDOL REACTION; BOND FORMATION; INTRAMOLECULAR REARRANGEMENT; EFFICIENT SYNTHESIS; COMPLEX CATALYSTS; MOLECULAR-OXYGEN; CO2; FIXATION; MALONIC-ACID; DERIVATIVES;

D O I：

10.1246/bcsj.20150043

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The gaseous carbon dioxide incorporation reaction with alpha,beta-unsaturated compounds was examined in the presence of a catalytic amount of bis(acetylacetonato)cobalt(II) and using diethylzinc as a reductant. After screening with various electron-withdrawing groups, both alpha,beta-unsaturated nitriles and carboxamides were found to efficiently capture carbon dioxide to provide the corresponding carboxylates or malonates in good to excellent yields under mild conditions.

引用

页码：862 / 870

页数：9

共 57 条

[1] Catalysis research of relevance to carbon management: Progress, challenges, and opportunities [J].

Arakawa, H ;

Aresta, M ;

Armor, JN ;

Barteau, MA ;

Beckman, EJ ;

Bell, AT ;

Bercaw, JE ;

Creutz, C ;

Dinjus, E ;

Dixon, DA ;

Domen, K ;

DuBois, DL ;

Eckert, J ;

Fujita, E ;

Gibson, DH ;

Goddard, WA ;

Goodman, DW ;

Keller, J ;

Kubas, GJ ;

Kung, HH ;

Lyons, JE ;

Manzer, LE ;

Marks, TJ ;

Morokuma, K ;

Nicholas, KM ;

Periana, R ;

Que, L ;

Rostrup-Nielson, J ;

Sachtler, WMH ;

Schmidt, LD ;

Sen, A ;

Somorjai, GA ;

Stair, PC ;

Stults, BR ;

Tumas, W .

CHEMICAL REVIEWS, 2001, 101 (04) :953-996

[2]

BASHA A, 1977, TETRAHEDRON LETT, P4171

[3] REACTIONS OF CARBON-DIOXIDE WITH CARBON CARBON BOND FORMATION CATALYZED BY TRANSITION-METAL COMPLEXES [J].

BRAUNSTEIN, P ;

MATT, D ;

NOBEL, D .

CHEMICAL REVIEWS, 1988, 88 (05) :747-764

[4] CATALYTIC, ENANTIOSELECTIVE ALDOL ADDITIONS WITH METHYL AND ETHYL-ACETATE O-SILYL ENOLATES - A CHIRAL TRIDENTATE CHELATE AS A LIGAND FOR TITANIUM(IV) [J].

CARREIRA, EM ;

SINGER, RA ;

LEE, WS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8837-8838

[5] C-2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of silylketene acetals to (benzyloxy)acetaldehyde [J].

Evans, DA ;

Murry, JA ;

Kozlowski, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (24) :5814-5815

[6] NICKEL EFFECT [J].

FISCHER, K ;

JONAS, K ;

MISBACH, P ;

STABBA, R ;

WILKE, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1973, 12 (12) :943-953

[7] Nickel-Catalyzed Double Carboxylation of Alkynes Employing Carbon Dioxide [J].

Fujihara, Tetsuaki ;

Horimoto, Yuichiro ;

Mizoe, Taiga ;

Sayyed, Fareed Bhasha ;

Tani, Yosuke ;

Terao, Jun ;

Sakaki, Shigeyoshi ;

Tsuji, Yasushi .

ORGANIC LETTERS, 2014, 16 (18) :4960-4963

[8] Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO2 [J].

Greenhalgh, Mark D. ;

Thomas, Stephen P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) :11900-11903

[9] Cobalt-catalyzed Reductive Carboxylation on α,β-Unsaturated Nitrites with Carbon Dioxide [J].

Hayashi, Chika ;

Hayashi, Takuo ;

Kikuchi, Satoshi ;

Yamada, Tohru .

CHEMISTRY LETTERS, 2014, 43 (04) :565-567

[10] Highly Practical Copper(I)/TEMPO Catalyst System for Chemoselective Aerobic Oxidation of Primary Alcohols [J].

Hoover, Jessica M. ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (42) :16901-16910

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