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Photocatalytic Synthesis of Oxetane Derivatives by Selective CH Activation
Author(s) -
Ravelli Davide,
Zoccolillo Matteo,
Mella Mariella,
Fagi Maurizio
Publication year - 2014
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.201400027
Subject(s) - oxetane , chemistry , chemoselectivity , photocatalysis , intramolecular force , radical , hydrogen atom abstraction , photochemistry , medicinal chemistry , combinatorial chemistry , stereochemistry , catalysis , organic chemistry
The selective C( sp 3 )H activation at position 2 in oxetanes has been accomplished by decatungstate photocatalysis under mild conditions. The resulting α‐oxy radicals were trapped by electron‐poor olefins resulting in the smooth preparation of 2‐substituted oxetanes. The chemoselectivity in hydrogen abstraction in substituted oxetanes containing other H donating groups, such as CH 2 OH, CH 2 OAc and CHO, has been demonstrated in intramolecular models.