Palladium(II)-Catalyzed meta-C-H Olefination: Constructing Multisubstituted Arenes through Homo-Diolefination and Sequential Hetero-Diolefination

被引：207

作者：

Bera, Milan ^{[1
]}

Maji, Arun ^{[1
]}

Sahoo, Santosh K. ^{[1
]}

Maiti, Debabrata ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 29期

关键词：

C-H activation; olefination; palladium; sulfur; synthetic methods; LATE-STAGE DIVERSIFICATION; ELECTRON-DEFICIENT ARENES; BOND ACTIVATION; HECK REACTION; DIRECTING GROUP; FUNCTIONALIZATION; ARYLATION; SELECTIVITY; CATALYST; REGIOSELECTIVITY;

D O I：

10.1002/anie.201503112

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Divinylbenzene derivatives represent an important class of molecular building blocks in organic chemistry and materials science. Reported herein is the palladium-catalyzed synthesis of divinylbenzenes by meta-C-H olefination of sulfone-based arenes. Successful sequential olefinations in a position-selective manner provided a novel route for the synthesis of hetero-dialkenylated products, which are difficult to access using conventional methods. Additionally, 1,3,5-trialkenylated compounds can be generated upon successful removal of the directing group.

引用

页码：8515 / 8519

页数：5

共 83 条

[1]

Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996

[2] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[3] Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].

Ackermann, Lutz .

CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877

[4] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[5] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[6]

[Anonymous], 2010, ANGEW CHEM

[7]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]

[8] Switching the Z/E Selectivity in the Palladium(II)-Catalyzed Decarboxylative Heck Arylations of trans-Cinnamaldehydes by Solvent [J].

Ban, Shu-Rong ;

Wang, Hai-Ning ;

Toader, Violeta ;

Bohle, D. Scott ;

Li, Chao-Jun .

ORGANIC LETTERS, 2014, 16 (24) :6282-6285

[9]

Beck E.M., 2008, ANGEW CHEM INT EDIT, V120, P3046

[10] Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy [J].

Beck, Elizabeth M. ;

Hatley, Richard ;

Gaunt, Matthew J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) :3004-3007

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