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A Mild Lewis‐Acid‐Catalyzed Method for Head‐to‐Tail Dimerization or Cyclization of tert ‐Alcohols
Author(s) -
Ramulu Bokka Venkat,
Mahendar Lodi,
Satyanarayana Gedu
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500456
Subject(s) - chemistry , regioselectivity , catalysis , lewis acids and bases , organic chemistry , friedel–crafts reaction , reaction conditions , medicinal chemistry , combinatorial chemistry
A mild and practical method is developed for the efficient synthesis of (1,1‐dimethyl‐3‐phenylbut‐3‐enyl)benzenes and indanes promoted by Lewis acid, starting from tert ‐benzyl alcohols. The reaction is temperature dependent and furnished the products with excellent regioselectivity. In the case of simple dimerization, Markovnikov head‐to‐tail coupling took place. On the other hand, reaction at elevated temperatures gave indanes through subsequent Friedel–Crafts cycloalkylation. Significantly, even electron‐rich aromatic systems were compatible for the formation of indanes, which would not be feasible by earlier reports, thus, revealing the advantage of the mild nature of the present protocol.