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Cyclopropanation/carboboration reactions of enynes with B(C6F5)3

Hansmann, Max M., Melen, Rebecca L., Rudolph, Matthias, Rominger, Frank, Waderpohl, Hubert, Stephan, Douglas W. and Hashmi, A. Stephen K. 2015. Cyclopropanation/carboboration reactions of enynes with B(C6F5)3. Journal of the American Chemical Society 137 (49) , pp. 15469-15477. 10.1021/jacs.5b09311

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Stoichiometric reaction of B(C6F5)3 with 1,6-enynes are shown to proceed via initial cyclopropanation and formal 1,1-carboboration. Depending on the substitution on the alkene moiety, subsequent ring-opening of the cyclopropane affords either cyclopentane or cyclohexane derivatives in which the C6F5 and B(C6F5)2 adopt a 1,4-positioning. Mechanistically this transformation involves π-activation of the alkyne moiety which triggers cyclopropanation, followed by carboboration. Both the cyclopropanation and subsequent ring-opening are shown to be stereospecific. Both cyclopropanation and 1,4-carboborated products were employed as Lewis acid components in frustrated Lewis pair activation of H2 and CO2.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes
Publisher: American Chemical Society
ISSN: 0002-7863
Date of First Compliant Deposit: 30 March 2016
Last Modified: 16 Sep 2020 16:15

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