Issue 28, 2006
From the journal:

Chemical Communications

Convenient synthesis of electron-donating substituted benzonitriles by photolysis of phenyl halides and esters†

Valentina Dichiarante,a   Maurizio Fagnoni*a  and  Angelo Albinia  

* Corresponding authors

a Department of Organic Chemistry, The University, V. Taramelli 10, Pavia, Italy
E-mail: fagnoni@unipv.it
Fax: +39 0382 987323
Tel: +39 0382 987316

Abstract

Irradiation of electron-donating substituted phenyl halides (fluorides and chlorides) or esters (mesylates, triflates and phosphates) in aqueous MeCN in the presence of KCN gives the corresponding benzonitriles in 48 to 100% yield through an ArSN1 reaction with the intermediacy of a triplet phenyl cation.

Graphical abstract: Convenient synthesis of electron-donating substituted benzonitriles by photolysis of phenyl halides and esters

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Article information

DOI
https://doi.org/10.1039/B605732B
Article type
Communication
Submitted
21 Apr 2006
Accepted
19 May 2006
First published
08 Jun 2006

Chem. Commun., 2006, 3001-3003

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Convenient synthesis of electron-donating substituted benzonitriles by photolysis of phenyl halides and esters

V. Dichiarante, M. Fagnoni and A. Albini, Chem. Commun., 2006, 3001 DOI: 10.1039/B605732B

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