Premium
Exploiting the Lithiation‐Directing Ability of Oxetane for the Regioselective Preparation of Functionalized 2‐Aryloxetane Scaffolds under Mild Conditions
Author(s) -
Coppi Donato Ivan,
Salomone Antonio,
Perna Filippo Maria,
Capriati Vito
Publication year - 2012
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.201109113
Subject(s) - oxetane , regioselectivity , metalation , borylation , chemistry , ring (chemistry) , combinatorial chemistry , polymer chemistry , organic chemistry , aryl , catalysis , alkyl
Oxetane nudges in the DoM direction! Regioselective ortho ‐lithiation induced by an oxetane ring has been achieved. The reaction provides easy access to ortho ‐functionalized 2‐aryloxetanes also through a lithiation/borylation Suzuki–Miyaura cross‐coupling. The lithiation‐directing ability of oxetane and the proton transfer mechanism have been investigated by competitive metalation and kinetic isotope effect studies.