Iron-catalyzed Chemoselective Cross-coupling of α-Bromocarboxylic Acid Derivatives with Aryl Grignard Reagents

被引：38

作者：

Jin, Masayoshi ^{[1
,2
]}

Nakamura, Masaharu ^{[1
]}

机构：

[1] Kyoto Univ, IRCELS, Inst Chem Res, Kyoto 6110011, Japan

[2] Daiichi Sankyo Co Ltd, Proc Technol Res Labs, Pharmaceut Technol Div, Hiratsuka, Kanagawa 2540014, Japan

来源：

CHEMISTRY LETTERS | 2011年 / 40卷 / 09期

基金：

日本学术振兴会;

关键词：

BEARING BETA-HYDROGENS; ALKYL-HALIDES; PALLADIUM; ARYLATION; ESTERS; COMPLEX; PHOSPHINE; ACETALS; KETONES;

D O I：

10.1246/cl.2011.1012

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a simple and effective synthetic method of alpha-arylcarboxylic acid derivatives based on the iron-catalyzed cross-coupling reaction of alpha-bromocarboxylic acid derivatives with aryl Grignard reagents. The reaction proceeds smoothly at -78 degrees C in a chemoselective manner to produce the coupling product in good to excellent yields.

引用

页码：1012 / 1014

页数：3

共 26 条

[1] Synthesis of new N-aryl oxindoles as intermediates for pharmacologically active compounds
Acemoglu, M
Allmendinger, T
Calienni, J
Cercus, J
Loiseleur, O
Sedelmeier, GH
Xu, D
[J]. TETRAHEDRON, 2004, 60 (50) : 11571 - 11586
[2] Synthesis of arylacetates by the palladium-catalyzed cross-coupling of aryl bromides and copper(II) enolates
Agnelli, F
Sulikowski, GA
[J]. TETRAHEDRON LETTERS, 1998, 39 (48) : 8807 - 8810
[3] Iron-phosphine, -phosphite, -arsine, and -carbene catalysts for the coupling of primary and secondary 2 alkyl halides with aryl Grignard reagents
Bedford, RB
Betham, M
Bruce, DW
Danopoulos, AA
Frost, RM
Hird, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03) : 1104 - 1110
[4] Iron(III) salen-type catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens
Bedford, RB
Bruce, DW
Frost, RM
Goodby, JW
Hird, M
[J]. CHEMICAL COMMUNICATIONS, 2004, (24) : 2822 - 2823
[5] Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens
Bedford, RB
Bruce, DW
Frost, RM
Hird, M
[J]. CHEMICAL COMMUNICATIONS, 2005, (33) : 4161 - 4163
[6] Iron-catalysed Suzuki coupling? A cautionary tale
Bedford, Robin B.
Nakamura, Masaharu
Gower, Nicholas J.
Haddow, Mairi F.
Hall, Mark A.
Huwe, Michael
Hashimoto, Tohru
Okopie, Rukeme A.
[J]. TETRAHEDRON LETTERS, 2009, 50 (45) : 6110 - 6111
[7] Selective Monoarylation of Acetate Esters and Aryl Methyl Ketones Using Aryl Chlorides
Biscoe, Mark R.
Buchwald, Stephen L.
[J]. ORGANIC LETTERS, 2009, 11 (08) : 1773 - 1775
[8] On the Role of Metal Contaminants in Catalyses with FeCl3
Buchwald, Stephen L.
Bolm, Carsten
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) : 5586 - 5587
[9] Iron-catalyzed alkylations of aromatic Grignard reagents
Cahiez, Gerard
Habiak, Vanessa
Duplais, Christophe
Moyeux, Alban
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (23) : 4364 - 4366
[10] PALLADIUM-CATALYZED COUPLING REACTIONS OF ARYL TRIFLATES OR HALIDES WITH KETENE TRIMETHYLSILYL ACETALS - A NEW ROUTE TO ALKYL 2-ARYLALKANOATES
CARFAGNA, C
MUSCO, A
SALLESE, G
SANTI, R
FIORANI, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) : 261 - 263

← 1 2 3 →