Transition-Metal-Catalyzed Site-Selective Cross-Coupling of Di- and Polyhalogenated Compounds

被引：101

作者：

Wang, Jia-Rui ^{[1
]}

Manabe, Kei ^{[1
]}

机构：

[1] RIKEN, Adv Sci Inst, Manabe Initiat Res Unit, Wako, Saitama 3510198, Japan

来源：

SYNTHESIS-STUTTGART | 2009年 / 09期

关键词：

cross-coupling; catalysis; halides; transition metals; site selectivity; TRISUBSTITUTED CONJUGATED DIENES; HIGHLY STEREOSELECTIVE-SYNTHESIS; DIELS-ALDER REACTION; ONE-POT SYNTHESIS; C-F ACTIVATION; GRIGNARD-REAGENTS; ARYL FLUORIDES; SUZUKI REACTION; STEREOCONTROLLED SYNTHESIS; REGIOSELECTIVE SYNTHESIS;

D O I：

10.1055/s-0029-1216632

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review highlights transition-metal-catalyzed cross-coupling reactions in which one of the halogen atoms (or pseudohalogen groups) of di- or polyhalogenated compounds is converted site-selectively into another group. The compounds are categorized as halogenated alkenes, heteroarene derivatives, benzene derivatives, and alkanes. Enantioselective cross-coupling of substrates having two enantiotopic halo groups is also described.

引用

页码：1405 / 1427

页数：23

共 118 条

[1] Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes [J].

Ackermann, Lutz ;

Althammer, Andreas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1627-1629

[2] Air-stable PinP(O)H as preligand for palladium-catalyzed Kumada couplings of unactivated tosylates [J].

Ackermann, Lutz ;

Althammer, Andreas .

ORGANIC LETTERS, 2006, 8 (16) :3457-3460

[3] Sterics versus electronics: Regioselective cross-coupling of polybrominated thiophenes [J].

Amb, Chad M. ;

Rasmussen, Seth C. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (05) :801-804

[4] Synthesis of the multisubstituted halogenated olefins via cross-coupling of dihaloalkenes with alkylzinc bromides [J].

Andrei, D ;

Wnuk, SF .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :405-408

[5] Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides:: p-orientation in the polyarylthiolation of polyfluorobenzenes [J].

Arisawa, Mieko ;

Suzuki, Takaaki ;

Ishikawa, Tomofumi ;

Yamaguchi, Masahiko .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12214-+

[6] Studies towards a postulated biomimetic Diels-Alder reaction for the synthesis of himgravine [J].

Baldwin, JE ;

Chesworth, R ;

Parker, JS ;

Russell, AT .

TETRAHEDRON LETTERS, 1995, 36 (52) :9551-9554

[7] Selective synthesis of (Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5H)-furanones [J].

Bellina, F ;

Anselmi, C ;

Viel, S ;

Mannina, L ;

Rossi, R .

TETRAHEDRON, 2001, 57 (50) :9997-10007

[8] Synthesis of 4-alkyl-3-bromo-2(5H)-furanones and unsymmetrically disubstituted 3,4-dialkyl-2(5H)-furanones by palladium-catalyzed cross-coupling reactions [J].

Bellina, F ;

Anselmi, C ;

Rossi, R .

TETRAHEDRON LETTERS, 2001, 42 (23) :3851-3854

[9] HIGHLY REGIOSELECTIVE PALLADIUM-MEDIATED SYNTHESIS OF STEREOISOMERICALLY PURE (Z)-ALKYL AND (E)-ALKYL 2-BROMO-3-(HETERO)ARYLPROPENOATES [J].

BELLINA, F ;

CARPITA, A ;

DESANTIS, M ;

ROSSI, R .

TETRAHEDRON LETTERS, 1994, 35 (37) :6913-6916

[10]

Blum J, 2000, SYNTHESIS-STUTTGART, P571

← 1 2 3 4 5 6 7 8 9 10 →