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Radical‐Mediated 1,2‐Formyl/Carbonyl Functionalization of Alkenes and Application to the Construction of Medium‐Sized Rings
Author(s) -
Li ZhongLiang,
Li XiaoHua,
Wang Na,
Yang NingYuan,
Liu XinYuan
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201608198
Subject(s) - heteroatom , radical , surface modification , chemistry , ring (chemistry) , selectivity , carbonyl group , functional group , combinatorial chemistry , photochemistry , medicinal chemistry , organic chemistry , catalysis , polymer
A novel radical 1,2‐formylfunctionalization of alkenes involving 1,2(4,5)‐formyl migration triggered by addition of various carbon‐ and heteroatom‐centered radicals to alkenes has been developed for the first time, thus providing straightforward access to diverse β‐functionalized aldehydes with good efficiency, remarkable selectivity, and excellent functional group tolerance. Analogous transformations mediated by a keto‐carbonyl migration have also been effected under similar conditions. This method was used to access ring systems including various benzannulated nine‐, ten‐, and eleven‐membered rings, complex 6‐5(6,7)‐6(5) fused rings, and bridged rings with diverse functionalities.