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Double FLP-Alkyne Exchange Reactions: A Facile Route to Te/B Heterocycles
Fu An Tsao1, Levy Cao1, Stefan Grimme2
1Department of Chemistry, University of Toronto , 80 St. George St., Toronto, Ontario Canada M5S 3H6.
Abstract:
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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