Iron-catalysed Negishi coupling of benzyl halides and phosphates

被引:154
作者
Bedford, Robin B. [1 ]
Huwe, Michael [1 ]
Wilkinson, Mark C. [2 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[2] GlaxoSmithKline Inc, Chem Dev, Stevenage SG1 2NY, Herts, England
基金
英国工程与自然科学研究理事会;
关键词
ARYL GRIGNARD-REAGENTS; SECONDARY ALKYL-HALIDES; BEARING BETA-HYDROGENS; DIHYDROFOLATE-REDUCTASE; ARYLBORONIC ACIDS; PNEUMOCYSTIS-CARINII; ARYLMAGNESIUM REAGENTS; MYCOBACTERIUM-AVIUM; TOXOPLASMA-GONDII; INHIBITORS;
D O I
10.1039/b818961g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Iron-based catalysts containing either 1,2-bis(diphenylphosphino)benzene or 1,3-bis(diphenylphosphino)propane give excellent activity and good selectivity in the Negishi coupling of aryl zinc reagents with a range of benzyl halides and phosphates.
引用
收藏
页码:600 / 602
页数:3
相关论文
共 36 条
[1]   MOSSBAUER AND PREPARATIVE STUDIES OF SOME IRON(II) COMPLEXES OF DIPHOSPHINES [J].
BARCLAY, JE ;
LEIGH, GJ ;
HOULTON, A ;
SILVER, J .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1988, (11) :2865-2870
[2]   Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents [J].
Bedford, RB ;
Betham, M ;
Bruce, DW ;
Davis, SA ;
Frost, RM ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2006, (13) :1398-1400
[3]   Iron-phosphine, -phosphite, -arsine, and -carbene catalysts for the coupling of primary and secondary 2 alkyl halides with aryl Grignard reagents [J].
Bedford, RB ;
Betham, M ;
Bruce, DW ;
Danopoulos, AA ;
Frost, RM ;
Hird, M .
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 [J].
Bedford, RB ;
Bruce, DW ;
Frost, RM ;
Goodby, JW ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2004, (24) :2822-2823
[5]   Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens [J].
Bedford, RB ;
Bruce, DW ;
Frost, RM ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2005, (33) :4161-4163
[6]   An iron-containing ionic liquid as recyclable catalyst for aryl grignard cross-coupling of alkyl halides [J].
Bica, K ;
Gaertner, P .
ORGANIC LETTERS, 2006, 8 (04) :733-735
[7]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[8]   Iron catalyzed polyethylene chain growth on zinc:: A study of the factors delineating chain transfer versus catalyzed chain growth in zinc and related metal alkyl systems [J].
Britovsek, GJP ;
Cohen, SA ;
Gibson, VC ;
van Meurs, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) :10701-10712
[9]   Simple palladium(II) precatalyst for Suzuki-Miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners [J].
Burns, Michael J. ;
Fairlamb, Ian J. S. ;
Kapdi, Anant R. ;
Sehnal, Petr ;
Taylor, Richard J. K. .
ORGANIC LETTERS, 2007, 9 (26) :5397-5400
[10]   Iron-catalyzed alkylation of alkenyl Grignard reagents [J].
Cahiez, Gerard ;
Duplais, Christophe ;
Moyeux, Alban .
ORGANIC LETTERS, 2007, 9 (17) :3253-3254