In this work, we demonstrate an NHC-mediated photoredox catalytic protocol that allows deoxygenative functionalization of a series of 1°,2°, and 3° alcohols with some electron-deficient radical acceptors, whereas, the in situ generated alcohol-NHC adducts could be converted into the alkyl radicals that were trapped by the sulfone-type electrophiles and trifluoromethyl alkenes. These operationally simple C-O bond functionalization approaches tolerate remarkably wide range of functional groups allowing access to important building blocks for drug discovery and medicinal chemistry. Moreover, it is described that the macrocyclic alkynes could also be prepared with high efficiency through the intramolecular deoxygenative alkynylation.

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