Synthesis 2017; 49(07): 1648-1654
DOI: 10.1055/s-0036-1588370
paper
© Georg Thieme Verlag Stuttgart · New York

Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid

Carlos M. Sanabria
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil   Email: luciasequeira@yahoo.com.br   Email: mmattos@iq.ufrj.br
,
Mariana T. do Casal
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil   Email: luciasequeira@yahoo.com.br   Email: mmattos@iq.ufrj.br
,
Raphael B. A. de Souza
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil   Email: luciasequeira@yahoo.com.br   Email: mmattos@iq.ufrj.br
,
Lúcia C. S. de Aguiar*
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil   Email: luciasequeira@yahoo.com.br   Email: mmattos@iq.ufrj.br
,
Marcio C. S. de Mattos*
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil   Email: luciasequeira@yahoo.com.br   Email: mmattos@iq.ufrj.br
› Author Affiliations
Further Information

Publication History

Received: 05 October 2016

Accepted after revision: 14 November 2016

Publication Date:
19 December 2016 (online)


Dedicated to the memory of Prof. José Barluenga

Abstract

An efficient regioselective iodination of N-phenylureas was developed using iodine/trichloroisocyanuric acid in acetonitrile at room temperature. This protocol proved to be effective on a broad range of substituted N-phenylureas, forming the p-iodinated compounds in 65–96% yield under mild and neutral conditions.

Supporting Information

 
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