Haloboration of internal alkynes with boronium and borenium cations as a route to tetrasubstituted alkenes

Lawson, James R., Clark, Ewan R., Cade, Ian A., Solomon, Sophia A., Ingleson, Michael J. (2013) Haloboration of internal alkynes with boronium and borenium cations as a route to tetrasubstituted alkenes. Angewandte Chemie International Edition, 52 (29). pp. 7518-7522. ISSN 1433-7851. (doi:10.1002/anie.201302609) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

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http://www.dx.doi.org/10.1002/anie.201302609

Abstract

Hail boration! 2-Dimethylaminopyridine-ligated dihaloborocations [X 2B(2-DMAP)]+ with a strained four-membered boracycle were used for the haloboration of terminal and dialkyl internal alkynes (see scheme). Esterification then provided vinyl boronate esters as useful precursors to tetrasubstituted alkenes. Following mechanistic studies, the scope of the haloboration was expanded simply by variation of the amine. Pin=2,3-dimethyl-2, 3-butanedioxy. © 2013 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of Creative Commons the Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.

Item Type: Article
DOI/Identification number: 10.1002/anie.201302609
Uncontrolled keywords: borenium ions, boronate esters, haloboration, synthetic methods, tetrasubstituted alkenes, Boronate esters, haloboration, Internal alkynes, Mechanistic studies, Synthetic methods, Tetrasubstituted alkenes, Vinyl boronate, Complexation, Esterification, Esters, Precipitation (meteorology), Hydrocarbons
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Sciences > School of Physical Sciences > Functional Materials Group
Depositing User: Giles Tarver
Date Deposited: 29 Jul 2015 15:10 UTC
Last Modified: 29 May 2019 14:56 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/49873 (The current URI for this page, for reference purposes)
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