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

被引：17

作者：

Barbero, Margherita ^{[1
]}

Cadamuro, Silvano ^{[1
]}

Dughera, Stefano ^{[1
]}

Rucci, Marta ^{[1
]}

Spano, Giulia ^{[1
]}

Venturello, Paolo ^{[1
]}

机构：

[1] Univ Turin, Dipartimento Chim, I-10125 Turin, Italy

来源：

TETRAHEDRON | 2014年 / 70卷 / 09期

关键词：

S(N)1-type reactions; Benzylic alcohols; Triarylmethanes; Nucleophilicity; Breasted acid catalyst; NUCLEOPHILIC-SUBSTITUTION-REACTIONS; FRIEDEL-CRAFTS ALKYLATIONS; BOND FORMATION; INDOLES; BENZYLATION; BENZHYDROLS; AROMATICS; ALDEHYDES; EFFICIENT;

D O I：

10.1016/j.tet.2014.01.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient alkylation of aromatic and heteroaromatic compounds via the direct S(N)1-type nucleophilic substitution of benzylic alcohols in the presence of catalytic amounts of the strong Bronsted 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. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1818 / 1826

页数：9

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