Pd-catalyzed O-arylation of ethyl acetohydroximate: synthesis of O-arylhydroxylamines and substituted benzofurans.
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.
Maimone
Thomas J
TJ
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Buchwald
Stephen L
SL
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D006877:Hydroxamic Acids / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D000588:Amines; D001572:Benzofurans; D006877:Hydroxamic Acids; D010165:Palladium; C553581:ethyl acetohydroximate