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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Bromide-bromate Couple of Varying Ratios for Bromination, Vicinal Functionalisation and Oxidation in a Clean Manner

Author(s): Subbarayappa Adimurthy, Brindaban C. Ranu, Gadde Ramachandraiah, Bishwajit Ganguly and Pushpito K. Ghosh

Volume 10 , Issue 6 , 2013

Page: [864 - 884] Pages: 21

DOI: 10.2174/157017941006140206102818

Price: $65

Abstract

The review highlights applications of bromide-bromate couple in organic synthesis. The couple having 5:1 mole ratio of bromide to bromate is useful for preparation of dibromo derivatives from alkenes/alkynes. The 2:1 couple affects substitution with high bromine atom efficiency. Vicinal functionalization of olefins has also been studied. The 1:8 bromide-bromate couple has proved promising in several oxidation reactions, the performance exceeding that of bromate alone. This reagent was also the most effective for deiodination of styrene-based iodohydrins with concomitant rearrangement by a novel pathway. In all the cases the reagents were activated through in situ acidification. The 5:1 reagent is obtained as intermediate during liquid bromine manufacture and the other reagents were prepared from it using ClO-. Liquid bromine could be avoided in the product life cycle.

Keywords: Bromide-bromate couples, direct preparation from bromine intermediate, In situ activation, reagents for green bromination and oxidation, regeneration and reuse.


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