Formal Carbene C-H Bond Insertion in the Cu(I)-Catalyzed Reaction of Bis(trimethylsilyl)diazomethane with Benzoxazoles and Oxazoles

A Cu(I)-catalyzed cross-coupling reaction of bis(trimethylsilyl)diazomethane and benzoxazoles/oxazoles is reported. A wide range of functional groups can be tolerated in this transformation. This reaction provides a new method to directly introduce a 1,1-bis(trimethylsilyl)methyl group into heteroaromatic C-H bonds. Subsequent transformations of 1,1-bis(trimethylsilyl)-methylated heteroaromatic compounds are also presented.