Synlett 2017; 28(09): 1071-1074
DOI: 10.1055/s-0036-1588143
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© Georg Thieme Verlag Stuttgart · New York

Regioselective Three-Component Coupling by the Palladium-Catalyzed Reaction of 2-Fluoroallylic Acetates with Phenols and Imides

Masaki Kogawa
Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan   Email: kawatsur@chs.nihon-u.ac.jp
,
Hirotaka Watanabe
Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan   Email: kawatsur@chs.nihon-u.ac.jp
,
Mitsuaki Yamamoto
Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan   Email: kawatsur@chs.nihon-u.ac.jp
,
Yukiko Tsuchi
Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan   Email: kawatsur@chs.nihon-u.ac.jp
,
Biao Zhou
Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan   Email: kawatsur@chs.nihon-u.ac.jp
,
Motoi Kawatsura*
Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan   Email: kawatsur@chs.nihon-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 21 December 2016

Accepted after revision: 11 January 2017

Publication Date:
02 February 2017 (online)


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Abstract

A palladium-catalyzed three-component coupling reaction of 2-fluoroallylic acetates with phenols, and imides is disclosed. The reaction was effectively catalyzed by [Pd(C3H5)Cl]2/DPPF in the presence of Cs2CO3, and phenols and imides were introduced onto the allyl unit through the C–F bond activation. Furthermore, the reaction proceeds with both high regioselectivity and high Z-selectivity.

Supporting Information