Iron-Catalyzed Suzuki-Miyaura Coupling of Alkyl Halides

被引：278

作者：

Hatakeyama, Takuji ^{[1
]}

Hashimoto, Toru ^{[1
,2
]}

Kondo, Yoshiyuki ^{[1
,2
]}

Fujiwara, Yuichi ^{[1
,2
]}

Seike, Hirofumi ^{[1
]}

Takaya, Hikaru ^{[1
]}

Tamada, Yoshinori

Ono, Teruo

Nakamura, Masaharu ^{[1
]}

机构：

[1] Kyoto Univ, Int Res Ctr Elements Sci, Inst Chem Res, IRCELS, Kyoto 6110011, Japan

[2] Kyoto Univ, Dept Energy & Hydrocarbon Chem, Grad Sch Engn, Kyoto 6110011, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 31期

基金：

日本学术振兴会;

关键词：

ARYL GRIGNARD-REAGENTS; LIVING RADICAL POLYMERIZATION; PARAMAGNETIC-SUSCEPTIBILITY; ORGANOBORON COMPOUNDS; ORGANIC-SYNTHESIS; BORONIC ACIDS; PHOSPHATES; ALKENYL; COBALT; REACTIVITY;

D O I：

10.1021/ja103973a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of novel iron(II) chloride-diphosphine complexes and magnesium bromide, lithium arylborates react with primary and secondary alkyl halides to give the corresponding coupling products in good to excellent yields. High functional group compatibility is also demonstrated in the reactions of substrates possessing reactive substituents, such as alkoxycarbonyl, cyano, and carbonyl groups.

引用

页码：10674 / 10676

页数：3

共 61 条

[1] 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

[2] Simple mixed Fe-Zn catalysts for the Suzuki couplings of tetraarylborates with benzyl halides and 2-halopyridines [J].

Bedford, Robin B. ;

Hall, Mark A. ;

Hodges, George R. ;

Huwe, Michael ;

Wilkinson, Mark C. .

CHEMICAL COMMUNICATIONS, 2009, (42) :6430-6432

[3] Iron-catalysed Suzuki coupling? A cautionary tale [J].

Bedford, Robin B. ;

Nakamura, Masaharu ;

Gower, Nicholas J. ;

Haddow, Mairi F. ;

Hall, Mark A. ;

Huwe, Michael ;

Hashimoto, Tohru ;

Okopie, Rukeme A. .

TETRAHEDRON LETTERS, 2009, 50 (45) :6110-6111

[4] Iron-catalysed Negishi coupling of benzyl halides and phosphates [J].

Bedford, Robin B. ;

Huwe, Michael ;

Wilkinson, Mark C. .

CHEMICAL COMMUNICATIONS, 2009, (05) :600-602

[5] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].

Bellina, F ;

Carpita, A ;

Rossi, R .

SYNTHESIS-STUTTGART, 2004, (15) :2419-2440

[6] Iron-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction (Retraction of vol 351, pg 1732, 2009) [J].

Bezier, David ;

Darcel, Christophe .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) :1081-1081

[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] Cationic 2,6-bis(imino)pyridine iron and cobalt complexes: synthesis, structures, ethylene polymerisation and ethylene/polar monomer co-polymerisation studies [J].

Britovsek, GJP ;

Gibson, VC ;

Spitzmesser, SK ;

Tellmann, KP ;

White, AJP ;

Williams, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2002, (06) :1159-1171

[9]

Cahiez G, 1998, SYNTHESIS-STUTTGART, P1199

[10] Iron-catalyzed alkenylation of Grignard reagents by enol phosphates [J].

Cahiez, Gerard ;

Gager, Olivier ;

Habiak, Vanessa .

SYNTHESIS-STUTTGART, 2008, (16) :2636-2644

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