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Diastereoselective Carbonyl Allylation with Simple Olefins Enabled by Palladium Complex-Catalyzed C-H Oxidative Borylation

Zhong-Lin Tao, Xing-Han Li, Zhi-Yong Han and Liu-Zhu Gong*

*Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China, Email: gonglzustc.edu.cn

Z.-L. Tao, X.-H. Li, Z.-Y. Han, L.-Z. Gong, J. Am. Chem. Soc., 2015, 137, 4054-4057.

DOI: 10.1021/jacs.5b00507 (free Supporting Information)


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Abstract

A highly diastereoselective Pd-catalyzed carbonyl allylation of aldehydes and isatins with simple acyclic olefins as allylating reagents consists of a Pd-catalyzed oxidative allylic C-H borylation and an allylboration of carbonyls accelerated by phosphoric acid. N-Fluorobenzenesulfonimide as oxidant plays a key role.

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Key Words

homoallylic alcohols, NFSI


ID: J48-Y2015