Synthesis 2016; 48(22): 3971-3975
DOI: 10.1055/s-0035-1562455
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot Aerobic Photooxidative Darzens Reaction from Styrene and Benzyl Alcohol via Phenacyl Iodide and Benzaldehyde by Using­ Iodine

Ryuji Omura
a   Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan
,
Akitoshi Fujiya
a   Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan
,
Eiji Yamaguchi
a   Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan
,
Norihiro Tada
a   Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan
,
Tsuyoshi Miura
b   Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Email: itoha@gifu-pu.ac.jp
,
Akichika Itoh*
a   Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan
› Author Affiliations
Further Information

Publication History

Received: 27 April 2016

Accepted after revision: 02 June 2016

Publication Date:
19 July 2016 (online)


Abstract

We report a one-pot protocol for the synthesis of α,β-epoxy ketones from benzyl alcohols and styrenes with molecular oxygen, visible light, and molecular iodine. This procedure involves simultaneous aerobic photooxidative transformation of a benzyl alcohol into a benzaldehyde and of a styrene into a phenacyl iodide, with a subsequent Darzens reaction in one pot. This is the first report of a one-pot oxidative Darzens reaction starting from benzyl alcohols and styrenes.

Supporting Information

 
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