Issue 3, 2011
From the journal:

Chemical Communications

Preparation of benzolactams by Pd(ii)-catalyzed carbonylation of N-unprotected arylethylamines†

Blanca López,a   Aleix Rodriguez,a   David Santos,a   Joan Albert,b   Xavier Ariza,a   Jordi Garcia*a  and  Jaume Granell*b  

* Corresponding authors

a Departament de Química Orgànica and IBUB, Fac. Química, Universitat de Barcelona, Martí i Franquès 1, 08028-Barcelona, Spain
E-mail: jordigarciagomez@ub.es
Fax: +34 93 3397878
Tel: +34 93 4034819

b Departament de Química Inorgànica and IBUB, Fac. Química, Universitat de Barcelona, Martí i Franquès 1, 08028-Barcelona, Spain
E-mail: jaume.granell@qi.ub.es
Fax: +34 93 4111492
Tel: +34 93 4039139

Abstract

An unprecedented NH2-directed Pd(II)-catalytic carbonylation of quaternary aromatic α-amino esters to yield 6-membered benzolactams has been developed. The reaction shows a strong bias to 6-membered lactams over 5-membered ones. The steric hindrance around the amino group seems to be pivotal for the success of the process.

Graphical abstract: Preparation of benzolactams by Pd(ii)-catalyzed carbonylation of N-unprotected arylethylamines

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Article information

DOI
https://doi.org/10.1039/C0CC03478A
Article type
Communication
Submitted
25 Aug 2010
Accepted
21 Oct 2010
First published
15 Nov 2010

Chem. Commun., 2011,47, 1054-1056

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Preparation of benzolactams by Pd(II)-catalyzed carbonylation of N-unprotected arylethylamines

B. López, A. Rodriguez, D. Santos, J. Albert, X. Ariza, J. Garcia and J. Granell, Chem. Commun., 2011, 47, 1054 DOI: 10.1039/C0CC03478A

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