Red Light-induced Conjugation of Amines Through Amide Bond Formation Triggered Via Photooxidation of 3-acylindolizines

Overview

Journal Commun Chem

Publisher Springer Nature

Specialty Chemistry

Date 2023 Jan 25

PMID 36697938

Authors

Kenji Watanabe

Asuka Kuratsu

Daisuke Hashizume

Takashi Niwa

Takamitsu Hosoya

Affiliations

Soon will be listed here.

Abstract

The development of a conjugation method initiated by irradiation of long-wavelength light (>500 nm) to prepare densely functionalized molecules while avoiding undesired photodegradation has attracted considerable attention. Here we show an amide bond formation method based on the photoreaction of 3-acylindolizines in the presence of amines triggered via red-light irradiation. Photooxidation of 3-acylindolizines using a catalytic amount of a photosensitizer and red light-emitting diodes (660 nm) affords the corresponding conjugated amides in nearly quantitative yields within <5 min. This transformation can be performed in aqueous organic solvents and is applicable to diverse aliphatic amines with various functional groups, including the moieties responsive to short-wavelength light.

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