Palladium/di-1-adamantyl-n-butylphosphine-catalyzed reductive carbonylation of aryl and vinyl halides

被引：78

作者：

Brennfuhrer, Anne ^{[1
]}

Neumann, Helfried ^{[1
]}

Klaus, Stefan ^{[1
]}

Riermeier, Thomas ^{[2
]}

Almena, Juan ^{[2
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany

[2] Degussa AG, D-63457 Hanau, Germany

来源：

TETRAHEDRON | 2007年 / 63卷 / 27期

关键词：

D O I：

10.1016/j.tet.2007.02.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and efficient palladium-catalyzed reductive carbonylation with low catalyst loadings (0.5 mol% Pd or below) has been developed. The formylation of aryl and heteroaryl bromides proceeds smoothly in the presence of palladium/di-1-adamantyl-n-butylphosphine at ambient pressure of synthesis gas to afford the corresponding aromatic aldehydes in good yields and excellent selectivity. In addition, vinyl halides react under similar conditions to form alpha,beta-unsaturated aldehydes in good yield. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6252 / 6258

页数：7

共 78 条

[1]

[Anonymous], 2013, ANGEW CHEM, V125, P4315, DOI DOI 10.1002/1521-3757(20001117)112:22

[2] NOVEL STEREOSPECIFIC ALKENYL-ALKENYL CROSS-COUPLING BY A PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTION OF ALKENYLALANES WITH ALKENYL HALIDES [J].

BABA, S ;

NEGISHI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6729-6731

[3] DIRECT CONVERSION OF ORGANIC HALIDES TO ALDEHYDES WITH CARBON-MONOXIDE AND TIN HYDRIDE CATALYZED BY PALLADIUM [J].

BAILLARGEON, VP ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (24) :7175-7176

[4] PALLADIUM-CATALYZED FORMYLATION OF ORGANIC HALIDES WITH CARBON-MONOXIDE AND TIN HYDRIDE [J].

BAILLARGEON, VP ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (03) :452-461

[5]

Beller M, 2001, CHIMIA, V55, P684

[6]

BELLER M, 2004, CHEM OGGI S CHIRAL C, V11, P16

[7] FORMYLATION OF ARYL CHLORIDES CATALYZED BY A PALLADIUM COMPLEX [J].

BENDAVID, Y ;

PORTNOY, M ;

MILSTEIN, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1816-1817

[8]

BLANCO L, 1981, SYNTHESIS-STUTTGART, P291

[9] Palladium-catalyzed synthesis of aldehydes from aryl iodides and acetic formic anhydride [J].

Cacchi, S ;

Fabrizi, G ;

Goggiamani, A .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (05) :692-694

[10] Formylation of aryl halides catalyzed by a silica-supported phosphine palladium complex [J].

Cai, MZ ;

Zhao, H ;

Zhou, J ;

Song, CS .

SYNTHETIC COMMUNICATIONS, 2002, 32 (06) :923-926

← 1 2 3 4 5 6 7 8 →