Visible-light-induced remote C(sp3)–H sulfonylvinylation: assembly of cyanoalkylated vinyl sulfones

A photoinduced sulfonylvinylation of unactivated C(sp3)–H bonds through a three-component reaction of propargyl alcohols, potassium metabisulfite and cycloketone oxime esters is developed. This approach enables rapid access to cyanoalkylated vinyl sulfones in moderate to good yields at room temperat...

Full description

Saved in:
Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2021-09, Vol.8 (17), p.4820-4825
Main Authors: Bao, Ping, Yu, Feiyan, Fu-Sheng, He, Tang, Zhimei, Wei-Ping, Deng, Wu, Jie
Format: Article
Language:English
Subjects:
Alcohols
Covalent bonds
Crystallography
Esters
Functional groups
Light effects
Organic chemistry
Oxime esters
Potassium
Potassium metabisulfite
Propargyl alcohol
Room temperature
Sulfones
Sulfur
Sulfur dioxide
Transition metals
Vinyl radical
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A photoinduced sulfonylvinylation of unactivated C(sp3)–H bonds through a three-component reaction of propargyl alcohols, potassium metabisulfite and cycloketone oxime esters is developed. This approach enables rapid access to cyanoalkylated vinyl sulfones in moderate to good yields at room temperature under transition-metal-free and external base-free conditions with the formation of three new C–SO2 and C–C bonds in one pot. A radical mechanism involving the insertion of sulfur dioxide with a cyanoalkyl radical and vinyl radical-triggered 1,5-hydrogen atom transfer and functional group migration sequence is proposed.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo00732g