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Gold‐Catalyzed Friedel–Crafts‐Like Reaction of Benzylic Alcohols to Afford 1,1‐Diarylalkanes
Author(s) -
Oakley James V.,
Stanley Tyler J.,
Jesse Kate A.,
Melanese Amanda K.,
Alvarez Araceli A.,
Prince Aloha L.,
Cain Stephanie E.,
Wenzel Anna G.,
Iafe Robert G.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901082
Subject(s) - friedel–crafts reaction , chemistry , regioselectivity , intramolecular force , catalysis , organic chemistry , combinatorial chemistry
A gold‐catalyzed, Friedel–Crafts‐like benzylation of unactivated benzylic alcohols to form 1,1‐diarylalkanes has been developed. The operationally convenient method uses only 1.3 equivalents of the electron‐rich arene, employs readily available starting materials, is highly reproducible, and is tolerant of moisture. Moderate‐to‐high product yields (34–99 %) with excellent regioselectivity were obtained. In particular, the intramolecular arylation of benzylic alcohols to afford substituted fluorenes represents a new avenue for gold research.