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Selective sp 3 C–H Bond Activation Based on a Carbocation Relay: Friedel–Crafts Reaction with Alkanes as the Alkylating Component
Author(s) -
Wang Jie,
Zhou Pengfei,
Wang Yang
Publication year - 2011
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.201001118
Subject(s) - carbocation , friedel–crafts reaction , chemistry , intramolecular force , naphthalene , alkane , selectivity , intramolecular reaction , organic chemistry , combinatorial chemistry , medicinal chemistry , photochemistry , catalysis
A highly efficient and selective intramolecular Friedel–Crafts reaction of 3‐methylbutyl or 4‐methylpentyl‐substituted aromatics has been developed using a carbocation relay strategy through selective sp 3 C–H bond activation, providing a facile and cost‐effective approach for the construction of benzocyclic compounds. A variety of 1,1‐dimethylindane and naphthalene derivatives have been prepared from very simple starting materials in good yields with high selectivity. The present strategy has provided a new example of a Friedel–Crafts reaction with alkanes as the alkylating component and constitutes a convenient approach to selective C–H bond activation and functionalization of alkane derivatives.