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Visible‐Light‐Mediated Nitrogen‐Centered Radical Strategy: Preparation of 3‐Acylated Spiro[4,5]trienones
Author(s) -
Chen Pu,
Xie Jun,
Chen Zan,
Xiong BiQuan,
Liu Yu,
Yang ChangAn,
Tang KeWen
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100852
Subject(s) - chemistry , acylation , oxime , alkyl , radical , aryl , nitrogen , carbon fibers , cleavage (geology) , aryl radical , organic chemistry , catalysis , materials science , geotechnical engineering , fracture (geology) , composite number , engineering , composite material
A nitrogen‐centered radical strategy for the preparation of 3‐acylated spiro[4,5]trienones via visible‐light‐mediated acylation/ ipso ‐cyclization of alkynes with acyl oxime esters is reported. The alkyl‐ and aryl‐substituted acyl radicals, which generate from the cleavage of carbon‐carbon σ ‐bonds in acyl oxime esters via nitrogen‐centered radical pathway, attack the carbon‐carbon triple bonds in propiolamides and then undergo ipso ‐cyclization. This method provides a way for the construction of 3‐acyl‐substituted spiro[4,5]trienones, which can introduce aryl‐ or alkyl‐substituted acyl into spiro[4,5]trienone skeletons.