Double FLP-Alkyne Exchange Reactions: A Facile Route to Te/B Heterocycles.

J Am Chem Soc

Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario Canada M5S 3H6.

Published: October 2015

1-Bora-4-tellurocyclohexa-2,5-diene undergoes sequential [4 + 2] cycloadditions/alkyne-elimination reactions to incorporate 2 equiv of terminal alkyne with the loss of diarylalkyne, affording access to a series of 11 new tellurium-boron heterocycles. These alkyne exchange reactions proceed regioselectively and can tolerate a variety of functional groups, thus providing the potential for further derivatization. The mechanism of the exchange reaction is confirmed by a DFT study to involve the interaction of the Te and B with the alkyne in a frustrated Lewis pair fashion in the transition states.

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http://dx.doi.org/10.1021/jacs.5b09526DOI Listing

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