An efficient Pd catalyst for the O-arylation of ethyl acetohydroximate with aryl chlorides, bromides, and iodides has been developed. Ethyl acetohydroximate serves as an efficient hydroxylamine equivalent for C−O cross-coupling, thereby allowing for the preparation of O-arylhydroxylamines from simple aryl halides. Short reaction times and broad substrate scope, including heteroaryl coupling partners, allow access to O-arylhydroxylamines that would be difficult to prepare in a single step by traditional methods. Moreover, the O-arylated products so formed can be directly transformed into substituted benzofurans in a single operation.
“Pd-Catalyzed O-Arylation of Ethyl Acetohydroximate: Synthesis of O-Arylhydroxylamines and Substituted Benzofurans”, J. Am. Chem. Soc., 2010, 132(29), 9990-9991.