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Synlett 2019; 30(11): 1366-1370
DOI: 10.1055/s-0037-1611538
letter
© Georg Thieme Verlag Stuttgart · New York

Alcohol-Directed ortho-C–H Alkenylation

Li Li
,
Qinglan Liu
,
Jiean Chen  *
State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Shenzhen 518055, P. R. of China   Email: chenja@pkusz.edu.cn   Email: huangyong@pkusz.edu.cn
,
Yong Huang  *
State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Shenzhen 518055, P. R. of China   Email: chenja@pkusz.edu.cn   Email: huangyong@pkusz.edu.cn
› Author AffiliationsThis work was financially supported by the National Natural Science Foundation of China (21825101, 21572004 for Y.H. and 21602007 for J.C.) and Shenzhen Science and Technology Innovation Commission (JCYJ20170818085510474, JCYJ20160226105602871, JCYJ20170818085438996).
Further Information

Publication History

Received: 26 March 2019

Accepted after revision: 24 April 2019

Publication Date:
21 May 2019 (online)

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Abstract

We report a simple and mild dehydrogenative cross-coupling reaction of unprotected arylethanols and acrylates. Unlike the case of previous reactions, in which prior functionalization of the substrate with a metal-coordinating site was required, free primary, secondary, or tertiary hydroxy groups were found to be effective directing groups for the ortho-C–H palladation and subsequent olefination.

Key words

directing group - palladium catalysis - cross-coupling - C–H activation - arylethanols - acrylates

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611538.
  • Supporting Information
 

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