Iron-Mediated Direct Suzuki-Miyaura Reaction: A New Method for the ortho-Arylation of Pyrrole and Pyridine

被引：106

作者：

Wen, Jun

Qin, Song

Ma, Li-Fang

Dong, Liang

Zhang, Ji

Liu, Shan-Shan

Duan, Yi-Shu

Chen, Shan-Yong

Hu, Chang-Wei ^{[1
]}

Yu, Xiao-Qi

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 12期

基金：

美国国家科学基金会;

关键词：

CROSS-COUPLING REACTIONS; C-H BOND; CATALYZED DIRECT ARYLATION; ALKYL-HALIDES; PALLADIUM; ACTIVATION; IRON(III); TRANSMETALATION; COMPLEXES; BASE;

D O I：

10.1021/ol100838m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of an iron-mediated direct Suzuki-Miyaura reaction between N-heterocyclic compounds and arylboronic acids is described, and both electron-rich and electron-deficient heteroarenes can be successfully used for the coupling reaction.

引用

页码：2694 / 2697

页数：4

共 63 条

[1] Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].

Berman, Ashley M. ;

Lewis, Jared C. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+

[2] 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

[3] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds [J].

Billingsley, Kelvin L. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) :3484-3488

[4] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[5] Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction [J].

Braga, AAC ;

Morgon, NH ;

Ujaque, G ;

Maseras, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9298-9307

[6] Computational study of the transmetalation process in the Suzuki-Miyaura cross-coupling of aryls [J].

Braga, Ataualpa A. C. ;

Morgon, Nelson H. ;

Ujaque, Gregori ;

Lledos, Agusti ;

Maseras, Feliu .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (21) :4459-4466

[7] On the Role of Metal Contaminants in Catalyses with FeCl3 [J].

Buchwald, Stephen L. ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5586-5587

[8] Efficient preparation of terminal conjugated dienes by coupling of dienol phosphates with Grignard reagents under iron catalysis [J].

Cahiez, Gerard ;

Habiak, Vanessa ;

Gager, Olivier .

ORGANIC LETTERS, 2008, 10 (12) :2389-2392

[9] Iron-catalyzed Sonogashira reactions [J].

Carril, Monica ;

Correa, Arkaitz ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) :4862-4865

[10] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

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