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Synlett 2024; 35(11): 1279-1284
DOI: 10.1055/a-2214-5512
cluster
Japan/Netherlands Gratama Workshop

Visible-Light-Induced Three-Component Radical Coupling of Selenocarbamates, Enones, and Allylstannanes with Diphenyl (2,4,6-trimethylbenzoyl)phosphine Oxide

Keita Komine
,
Yuta Yamazaki
,
Taiga Iwanaga
,
Hikaru Sakaguchi
,
Hayato Fukuda
,
Jun Ishihara  ∗
This work was supported by JSPS KAKENHI grants numbers 22K15254 (K.K.) and 23K04736 (J.I.). This work was the result of using research equipment shared in MEXT project for promoting public utilization of advanced research infrastructure (program for supporting introduction of the new sharing system) Grant Number JPMXS0422500320.
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Abstract

A blue LED-induced three-component coupling of a carbamoyl radical, cyclic enone, and allylstannane was developed. The use of blue LEDs and diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) as a radical initiator permitted the three-component radical coupling to proceed with a high chemoselectivity. An elucidation of the mechanism revealed a pathway for the formation of a tributyltin radical from TPO and allylstannane. This tandem radical reaction is expected to be applicable in natural-product synthesis.

Key words

radical reaction - coupling - multicomponent reaction - photochemical reaction - total synthesis - amides

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2214-5512.
  • Supporting Information


Publikationsverlauf

Eingereicht: 31. Oktober 2023

Angenommen nach Revision: 20. November 2023

Accepted Manuscript online:
20. November 2023

Artikel online veröffentlicht:
21. Dezember 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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