American Chemical Society
ja5b09526_si_001.pdf (1.08 MB)

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

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journal contribution
posted on 2015-10-21, 00:00 authored by Fu An Tsao, Levy Cao, Stefan Grimme, Douglas W. Stephan
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.