Activation of alkynes with B(C6F5)3 – boron allylation reagents derived from propargyl esters

Hansmann, Max M., Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831, Rominger, Frank, Hashmi, A. Stephen K. and Stephan, Douglas W. 2014. Activation of alkynes with B(C6F5)3 – boron allylation reagents derived from propargyl esters. Journal of the American Chemical Society 136 (2) , pp. 777-782. 10.1021/ja4110842

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Abstract

Novel allyl boron compounds are readily synthesized via rearrangement reactions between Lewis acidic B(C6F5)3 and propargyl esters. These reactions proceed through an initial cyclization followed by ring-opening and concurrent C6F5-group migration. In the absence of disubstitution adjacent to the ester oxygen atom, an allyl boron migration rearrangement leads to formal 1,3-carboboration products. These allyl boron compounds act as allylation reagents with aldehydes introducing both a C3-allyl fragment and a C6F5-unit as a single anti-diastereomer. In these reactions, B(C6F5)3 activates the alkynes, prompting the rearrangement processes and enabling installations of C6F5 and R-groups.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	American Chemical Society
ISSN:	0002-7863
Last Modified:	27 Oct 2022 09:16
URI:	https://orca.cardiff.ac.uk/id/eprint/65038

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