Reductive Dehalogenation of
Aryl Bromides and Chlorides and Their Use as Aryl Blocking Groups

Ahalya Ramanathan; Leslie S. Jimenez

doi:10.1055/s-0029-1217112

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Synthesis 2010(2): 217-220
DOI: 10.1055/s-0029-1217112

PAPER

Reductive Dehalogenation of Aryl Bromides and Chlorides and Their Use as Aryl Blocking Groups

Ahalya Ramanathan, Leslie S. Jimenez*
Department of Chemistry & Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854-8087, USA
Fax: +1(732)4455312; e-Mail: Leslie.Jimenez@rutgers.edu;

Further Information

Publication History

Received 7 August 2009
Publication Date:
13 November 2009 (online)

Abstract
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Abstract

Bromo and chloro substituents serve as excellent blocking groups on aromatic rings. When a halo substituent is para to an ortho,para-directing group, the ortho positions can be easily functionalized, and the halo group can be subsequently removed by catalytic hydrogenation under neutral conditions. As expected, bromides are reduced more quickly than chlorides and the reaction requires the use of less catalyst. Bromides can be selectively reduced in the presence of nitro, chloro, cyano, keto, or carboxylic acid groups.

Key words

arenes - halides - hydrogenation - reductions - regioselectivity

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