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Branch-Selective Allylic C-H Carboxylation of Terminal Alkenes by Pd/sox Catalyst

Hiroki Kondo, Feng Yu, Junichiro Yamaguchi, Guosheng Liu* and Kenichiro Itami*

*Shanghai Institute of Organic Chemistry, Shanghai 200032, China; Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan, Email: gliumail.sioc.ac.cn, itamichem.nagoya-u.ac.jp

H. Kondo, F. Yu, J. Yamaguchi, G. Liu, K. Itami, Org. Lett., 2014, 16, 4212-4215.

DOI: 10.1021/ol5019135  (free Supporting Information)


Abstract

Pd(OAc)2, sulfoxide-oxazoline (sox) as a ligand and benzoquinone as an oxidant enable a ligand-controlled branch-selective allylic C-H carboxylation. The developed catalytic system couples terminal alkenes and carboxylic acids to furnish the corresponding branched allylic esters with high regioselectivity.

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Key Words

allylic alcohols, benzoquinone


ID: J54-Y2014