Ligand-Free Pd-Catalyzed Highly Selective Arylation of Allylic Esters with Retention of the Traditional Leaving Group

What leaving group? Organic halides and allylic esters undergo efficient Pd‐catalyzed Heck reactions under mild conditions in air to form a new CC bond without elimination of the β‐OAc group in the intermediate palladium complex. Instead a highly regioselective β‐H elimination takes place to provid...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-06, Vol.47 (25), p.4729-4732
Main Authors: Pan, Delin, Chen, Anjun, Su, Yijin, Zhou, Wang, Li, Si, Jia, Wei, Xiao, Juan, Liu, Qingjian, Zhang, Liangren, Jiao, Ning
Format: Article
Language:English
Subjects:
allylic compounds
Catalysis
Esters - chemistry
Heck reaction
Ligands
Models, Chemical
palladium
Palladium - chemistry
Propanols - chemistry
regioselectivity
silver
Silver - chemistry
Stereoisomerism
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Summary:What leaving group? Organic halides and allylic esters undergo efficient Pd‐catalyzed Heck reactions under mild conditions in air to form a new CC bond without elimination of the β‐OAc group in the intermediate palladium complex. Instead a highly regioselective β‐H elimination takes place to provide substituted derivatives of allylic alcohols (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200800966