Issue 17, 2015

Chemo-, regio-, and stereoselective Heck–Matsuda arylation of allylic alcohols under mild conditions

Abstract

Heck arylation with allylic alcohol is extremely challenging due to chemo-, regio-, and stereoselective scrambling. Here we report a mild protocol for the alcohol selective β- and α-arylation of allylic and cinnamyl alcohols respectively with aryldiazonium salts. The steric and electronic parameters of the alkene play a prominent role in the regioselectivity.

Graphical abstract: Chemo-, regio-, and stereoselective Heck–Matsuda arylation of allylic alcohols under mild conditions

Supplementary files

Article information

Article type
Communication
Submitted
03 Feb 2015
Accepted
19 Mar 2015
First published
19 Mar 2015

Org. Biomol. Chem., 2015,13, 4841-4845

Author version available

Chemo-, regio-, and stereoselective Heck–Matsuda arylation of allylic alcohols under mild conditions

T. Y. Chaudhari, A. Hossian, M. K. Manna and R. Jana, Org. Biomol. Chem., 2015, 13, 4841 DOI: 10.1039/C5OB00235D

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