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Palladium-Catalyzed Aryl C-H Olefination with Unactivated, Aliphatic Alkenes

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Title Palladium-Catalyzed Aryl C-H Olefination with Unactivated, Aliphatic Alkenes
 
Creator DEB, A
BAG, S
KANCHERLA, R
MAITI, D
 
Subject BIDENTATE-CHELATION ASSISTANCE
OXIDIZING DIRECTING GROUP
CROSS-COUPLING REACTIONS
CARBON-HYDROGEN BONDS
HECK REACTION
OXIDATIVE OLEFINATION
DIRECT ARYLATION
CONJUGATED POLYMERS
ACID-DERIVATIVES
PD(II)-CATALYZED OLEFINATION
 
Description Palladium-catalyzed coupling between aryl halides and alkenes (Mizoroki-Heck reaction) is one of the most popular reactions for synthesizing complex organic molecules. The limited availability, problematic synthesis, and higher cost of aryl halide precursors (or their equivalents) have encouraged exploration of direct olefination of aryl carbon-hydrogen (C-H) bonds (Fujiwara-Moritani reaction). Despite significant progress, the restricted substrate scope, in particular noncompliance of unactivated aliphatic olefins, has discouraged the use of this greener alternative. Overcoming this serious limitation, we report here a palladium-catalyzed chelation-assisted ortho C-H bond olefination of phenylacetic acid derivatives with unactivated, aliphatic alkenes in good to excellent yields with high regio- and stereoselectivities. The versatility of this operationally simple method has been demonstrated through drug diversification and sequential C-H olefination for synthesizing divinylbenzene derivatives.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-12-29T05:43:51Z
2014-12-29T05:43:51Z
2014
 
Type Article
 
Identifier JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 136(39)13602-13605
0002-7863
http://dx.doi.org/10.1021/ja5082734
http://dspace.library.iitb.ac.in/jspui/handle/100/17224
 
Language English