Gold‐Catalyzed Friedel–Crafts‐Like Reaction of Benzylic Alcohols to Afford 1,1‐Diarylalkanes

• Published in: European journal of organic chemistry Vol. 2019; no. 42; pp. 7063 - 7066
• Main Authors: 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.
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 14-11-2019
• Subjects: Alcohol; Alcohols; Diarylalkanes; Electrophilic substitution; Fluorene synthesis; Friedel-Crafts reaction; Gold; Regioselectivity
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201901082

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.
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 electron‐rich arene, employs readily available starting materials, is highly reproducible, and is tolerant to moisture. Moderate‐to‐high product yields (34–99 %) with excellent regioselectivity were obtained.