Photocatalytic Aldehyde C−H Bond Phosphonioethylation with Vinylphosphonium Bromide

Author:

Mori Haruna1,Yoshida Masaki1,Sawamura Masaya12ORCID,Masuda Yusuke1ORCID

Affiliation:

1. Department of Chemistry Faculty of Science Hokkaido University Kita 10 Nishi 8, Kita-ku 060-0810 Sapporo Hokkaido Japan

2. Institute for Chemical Reaction Design and Discovery (WPI-ICReDD) Hokkaido University Kita 21 Nishi 10, Kita-ku 001-0021 Sapporo Hokkaido Japan

Abstract

AbstractPhotocatalytic C−H bond phosphonioethylation of aldehydes with vinylphosphonium bromide has been developed. Various β‐phosphonioalkylketones are synthesized from readily available aldehydes under neutral conditions. Mechanistic studies suggest that C−H activation of aldehydes occurs through hydrogen‐atom transfer by a bromine radical and that an alcoholic additive, which showed marked effects in increasing the efficiency of the reaction, is involved in the reaction as a proton source.

Publisher

Wiley

Subject

Organic Chemistry

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