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σ- versus π-activation of alkynyl benzoates using B(C6F5)3

Bähr, Alexander, Wilkins, Lewis, Ollegott, Kevin, Kariuki, Benson and Melen, Rebecca L. 2015. σ- versus π-activation of alkynyl benzoates using B(C6F5)3. Molecules 20 (3) , pp. 4530-4547. 10.3390/molecules20034530

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We have prepared a range of alkynyl benzoates in high yields and have investigated their reactivities with the strong Lewis acid B(C6F5)3. In such molecules both σ-activation of the carbonyl and π-activation of the alkyne are possible. In contrast to the reactivity of propargyl esters with B(C6F5)3 which proceed via 1,2-addition of the ester and B(C6F5)3 across the alkyne, the inclusion of an additional CH2 spacer switches off the intramolecular cyclization and selective σ-activation of the carbonyl group is observed through adduct formation. This change in reactivity appears due to the instability of the species which would be formed through B(C6F5)3 activation of the alkyne.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: boron; trispentafluorophenyl borane; B(C6F5)3; Lewis acid; alkyne
Publisher: MDPI AG
ISSN: 1420-3049
Date of First Compliant Deposit: 18 April 2017
Date of Acceptance: 28 February 2015
Last Modified: 17 Oct 2019 02:38

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