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Friedel–Crafts Benzylation of Activated and Deactivated Arenes
Author(s) -
Schäfer Gabriel,
Bode Jeffrey W.
Publication year - 2011
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.201105380
Subject(s) - friedel–crafts reaction , carbocation , substrate (aquarium) , chemistry , organic chemistry , medicinal chemistry , catalysis , geology , oceanography
NO going back makes possible facile Friedel–Crafts benzylations with moderate reaction temperatures, simple reaction workups, and improved substrate scope for the formation of synthetically important diarylmethanes (see scheme). Upon complexation with BF 3 ⋅OEt 2 , hydroxamates serve as reversible leaving groups that stabilize highly reactive carbocations. Even deactivated arenes and electron‐deficient benzylhydroxamates react cleanly under these conditions.