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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. ORCID: https://orcid.org/0000-0003-3142-2831 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: 26 Nov 2022 17:15
URI: https://orca.cardiff.ac.uk/id/eprint/94186

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