Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 41, Pages 13264-13267Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b09526
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Funding
- Canadian Foundation for Innovation [19119]
- Ontario Research Fund
- NSERC of Canada
- Canada Research Chair
- DFG
- NSERC CGS-D
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1-Bora-4-tellurocydohexa-2,5-diene undergoes sequential [4 + 2] cydoadditions/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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