A simple and efficient alkylation of aromatic and heteroaromatic compounds via the direct SN1-type nucleophilic substitution of benzylic alcohols in the presence of catalytic amounts of the strong Brønsted acid o-benzenedisulfonimide under neat conditions is herein reported. A library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and high regioselectivity. The observed reactivity was shown to be in agreement with Mayr’s nucleophilicity and electrophilicity scales.

Solvent-free Brønsted acid catalysed alkylation of arenes and heteroarenes with benzylic alcohols

BARBERO, Margherita;CADAMURO, Silvano;DUGHERA, Stefano;VENTURELLO, Paolo
2014-01-01

Abstract

A simple and efficient alkylation of aromatic and heteroaromatic compounds via the direct SN1-type nucleophilic substitution of benzylic alcohols in the presence of catalytic amounts of the strong Brønsted acid o-benzenedisulfonimide under neat conditions is herein reported. A library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and high regioselectivity. The observed reactivity was shown to be in agreement with Mayr’s nucleophilicity and electrophilicity scales.
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1818
1826
http://www.journals.elsevier.com/tetrahedron/
SN1-type reactions; benzylyc alcohols; triarylmethanes; Bronsted acid catalyst; nucleophilicity
Margherita Barbero; Silvano Cadamuro; Stefano Dughera; Marta Rucci; Giulia Spano; Paolo Venturello
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/143530
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