Photocatalytic Addition Reactions of Ketene Silyl Acetals with Alkenes through Formation of α‐Carbonyl Radicals

Addition reactions of ketene silyl acetals with alkenes that do not have an electron‐withdrawing group are generally difficult because the nucleophilicity of ketene silyl acetals and the electrophilicity of alkenes are not sufficient. Herein, we report photocatalytic addition reactions of ketene sil...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2022-10, Vol.17 (19), p.e202200647-n/a
Main Authors: Hirata, Tsubasa, Ogasawara, Yoshihiro, Kobayashi, Shū, Yamashita, Yasuhiro
Format: Article
Language:English
Subjects:
Acetals
alkene
Alkenes
alkylation
Carbonyls
Chemistry
ketene silyl acetal
Light irradiation
photoredox catalyst
visible light
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Addition reactions of ketene silyl acetals with alkenes that do not have an electron‐withdrawing group are generally difficult because the nucleophilicity of ketene silyl acetals and the electrophilicity of alkenes are not sufficient. Herein, we report photocatalytic addition reactions of ketene silyl acetals with alkenes that proceed through formation of α‐carbonyl radicals. In the presence of an appropriate protic additive, the reactions proceeded smoothly under blue‐light irradiation to afford the desired products in moderate to high yields. Photocatalytic addition reactions of ketene silyl acetals with alkenes bearing no electron‐withdrawing group are reported. By using appropriate protic additives, the desired reactions proceeded smoothly to afford the desired products through formation of α‐carbonyl radicals.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.202200647