Pd-Catalyzed Threefold Arylation of Baylis-Hillman Bromides and Acetates with Triarylbismuth Reagents

被引：14

作者：

Rao, Maddali L. N. ^{[1
]}

Giri, Somnath ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 24期

关键词：

Bismuth; Palladium; Alkenes; Synthetic methods; C-C coupling; OXIDATIVE HECK REACTIONS; EFFICIENT SYNTHESIS; ALLYLIC COMPOUNDS; ASYMMETRIC-SYNTHESIS; BETA(2)-AMINO ACIDS; PROTEASE INHIBITORS; DIRECT INSERTION; 3+2 ANNULATION; RAPID ACCESS; PALLADIUM;

D O I：

10.1002/ejoc.201200543

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized alkyl 2-benzylacrylates and 2-benzylacrylonitriles were synthesized by means of atom-economic cross-couplings of BaylisHillman bromides or acetates with BiAr3 under palladium-catalyzed conditions. These reactions, involving threefold aryl couplings using BiAr3 reagents with bromides and acetates, are fast and are completed in 12 h with high product yields.

引用

页码：4580 / 4589

页数：10

共 80 条

[1] ALPHA-METHYLENIC AND ALPHA-HYDROXYMETHYLATED ESTERS PREPARED BY THE ADDITION OF ORGANOLITHIUM OR MAGNESIUM ON ETHYL ALPHA-(HYDROXYMETHYL)ACRYLATE AND ITS DERIVATIVES IN THE PRESENCE OF COPPER(I) [J].

AMRI, H ;

RAMBAUD, M ;

VILLIERAS, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 308 (03) :C27-C32

[2] ALPHA-(METHYLENE)ALKANOIC ESTERS VIA SUBSTITUTIONS OF ETHERS AND ACIDS DERIVED FROM ETHYL ALPHA-(HYDROXYMETHYL)ACRYLATE [J].

AMRI, H ;

RAMBAUD, M ;

VILLIERAS, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 384 (1-2) :1-11

[3] Preparation and selective reactions of mixed bimetallic aromatic and heteroaromatic boron-magnesium reagents [J].

Baron, O ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (20) :3133-3135

[4] THE CHEMISTRY OF ORGANOBISMUTH REAGENTS .13. LIGAND COUPLING INDUCED BY PD(0) [J].

BARTON, DHR ;

OZBALIK, N ;

RAMESH, M .

TETRAHEDRON, 1988, 44 (18) :5661-5668

[5] The Baylis-Hillman chemistry in aqueous media: a convenient synthesis of 2-methylenealkanoates and alkanenitriles [J].

Basavaiah, D ;

Kumaragurubaran, N .

TETRAHEDRON LETTERS, 2001, 42 (03) :477-479

[6] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[7] The aqueous trimethylamine mediated Baylis-Hillman reaction [J].

Basavaiah, D ;

Krishnamacharyulu, M ;

Rao, AJ .

SYNTHETIC COMMUNICATIONS, 2000, 30 (11) :2061-2069

[8] Dimethyl sulfide induced [3+2] annulation strategy: An efficient synthesis of functionalized dihydropyrazole derivatives using the Baylis-Hillman bromides [J].

Basavaiah, Deevi ;

Roy, Suparna .

ORGANIC LETTERS, 2008, 10 (09) :1819-1821

[9] An expedient, facile and simple one-pot synthesis of 2-methylenealkanoates and alkanenitriles from the Baylis-Hillman bromides in aqueous media [J].

Basavaiah, Deevi ;

Reddy, Kanumuri Ramesh ;

Kumaragurubaran, Nagaswamy .

NATURE PROTOCOLS, 2007, 2 (11) :2665-2676

[10] The Baylis-Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry [J].

Basavaiah, Deevi ;

Rao, Kalapala Venkateswara ;

Reddy, Raju Jannapu .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1581-1588

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