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Factors affecting migration of tertiary alkyl groups in reactions of alkylboronic esters with bromomethyllithium

Elliott, Mark Christopher, Smith, Keith, Jones, Dyfyr Heulyn, Hussain, Aja and Saleh, Basil A. 2013. Factors affecting migration of tertiary alkyl groups in reactions of alkylboronic esters with bromomethyllithium. The Journal of Organic Chemistry 78 (7) , pp. 3057-3064. 10.1021/jo4000459

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Abstract

The reactions of bromomethyllithium with tert-alkylboronic esters could be of great potential for the formation of quaternary carbon centers, but often give poor yields/conversions. Calculations and experimental evidence show that tert-alkyl groups migrate less effectively than other types of alkyl group in such reactions, and that O migration competes. Furthermore, slow/incomplete capture of the bromomethyl reagent by the boronic ester is a problem in more hindered systems, and an additional competing reaction, possibly Li-Br exchange on the bromomethylborate species, also leads to lower yields of migrated products. Based on this, experimental protocols have been devised in which the competing reactions are largely suppressed, leading to higher conversions to migrated product for several substrates.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 0022-3263
Last Modified: 04 Jun 2017 04:42
URI: http://orca.cf.ac.uk/id/eprint/43356

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