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The propargyl rearrangement to functionalised allyl-boron and borocation compounds

Wilkins, Lewis C., Lawson, James R., Wieneke, Philipp, Rominger, Frank, Hashmi, A. Stephen K., Hansmann, Max M. and Melen, Rebecca L. 2016. The propargyl rearrangement to functionalised allyl-boron and borocation compounds. Chemistry - a European Journal 22 (41) , pp. 14618-14624. 10.1002/chem.201602719

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Abstract

A diverse range of Lewis acidic alkyl, vinyl and aryl boranes and borenium compounds that are capable of new carbon–carbon bond formation through selective migratory group transfer have been synthesised. Utilising a series of heteroleptic boranes [PhB(C6F5)2 (1), PhCH2CH2B(C6F5)2 (2), and E-B(C6F5)2(C6F5)C=C(I)R (R=Ph 3 a, nBu 3 b)] and borenium cations [phenylquinolatoborenium cation ([QOBPh][AlCl4], 4)], it has been shown that these boron-based compounds are capable of producing novel allyl- boron and boronium compounds through complex rearrangement reactions with various propargyl esters and carbamates. These reactions yield highly functionalised, synthetically useful boron substituted organic compounds with substantial molecular complexity in a one-pot reaction.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Wiley Blackwell
ISSN: 0947-6539
Funders: EPSRC
Date of First Compliant Deposit: 5 September 2016
Date of Acceptance: 19 August 2016
Last Modified: 02 Nov 2017 19:20
URI: http://orca.cf.ac.uk/id/eprint/94186

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