Regioselective Control of Electrophilic Aromatic Substitution Reactions

Authors: Smith K.; El-Hiti G.A.

Source: Current Organic Synthesis, Volume 1, Number 3, July 2004 , pp. 253-274(22)

Publisher: Bentham Science Publishers

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Abstract:

para-Regioselective electrophilic aromatic substitution reactions, for example nitration, alkylation, acylation, sulfonylation and halogenation, can be achieved by carrying out reactions over solid catalysts such as zeolites, under modest conditions via shape-selectivity. By contrast, organolithium reagents can play an important role when ortho-products are desirable. ortho-Lithiation has been applied for the synthesis of more complex substituted heterocycles that are difficult to prepare by other means.

Keywords: regioisomers; zeolites; electrophilic aromatic substitution reactions; directed lithiation; shape selectivity; heterocycles

Document Type: Review article

DOI: http://dx.doi.org/10.2174/1570179043366747

Affiliations: 1: Centre for Clean Chemistry, Department of Chemistry, University of Wales Swansea, Singleton Park, Swansea, SA2 8PP, UK

Publication date: 2004-07-01

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Current Organic Synthesis publishes in-depth reviews on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.