Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Hypervalent Iodonium Alkynyl Triflate Generated Phenylcyanocarbene and Its Reactivity with Aromatic Systems

Hypervalent Iodonium Alkynyl Triflate Generated Phenylcyanocarbene and Its Reactivity with Aromatic Systems
Mitchell P. Croatt, A. Christina Hairston, James A. Carson, Mohammed H. Al-Huniti, I. F. Dempsey Hyatt, Jarrod L. Stanley, Zachary B. Sullivan
Phenylcyanocarbene was generated by the reaction of azide with a hypervalent iodonium alkynyl triflate and reacted in situ with 21 different carbocyclic and heterocyclic aromatic compounds. These reactions led to more complex products that frequently underwent subsequent rearrangements. The reactivity was further explored in a mechanistic study to ascertain the chemoselectivity and stereospecificity.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01608

DOI: 10.1021/acs.joc.7b01608

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