Direct Synthesis of Enones by Visible-Light-Promoted Oxygenation of Trisubstituted Olefins Using Molecular Oxygen

Author:

Harada Shinji12ORCID,Matsuda Daiki1,Morikawa Takahiro1,Nishida Atsushi1

Affiliation:

1. Graduate School of Pharmaceutical Sciences, Chiba University

2. Molecular Chirality Research Center, Chiba University

Abstract

A one-step synthesis of enones from olefins is described. The reaction was performed under visible-light irradiation in the presence of molecular oxygen and a photocatalyst. The reaction proceeded with various types of trisubstituted olefins to give enones in good yields with high regioselectivity. In particular, oxygen- and nitrogen-containing functional groups, heteroaromatic rings, and cyclopropanes were tolerated. Mechanistic studies and previous reports indicated that the active oxygen species generated in the reaction system is singlet oxygen.

Funder

Japan Society for the Promotion of Science

Tokyo Biochemical Research Foundation

Sumitomo Foundation

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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