Direct Preparation of Benzofurans from O-Arylhydroxylamines
Fanny Contiero, Kevin M. Jones, Edward A. Matts, Achim Porzelle, Nicholas C. O. Tomkinson*
*School of Chemistry, Main Building, Cardiff University, Park
Place, Cardiff, CF10 3AT, UK, Email: tomkinsonnc
cardiff.ac.uk
F. Contiero, K. M. Jones, E. A. Matts, A. Porzelle, N. C. O. Tomkinson, Synlett, 2009, 3003-3006.
DOI: 10.1055/s-0029-1218273
Abstract
Reaction of O-arylhydroxylamine hydrochlorides with either cyclic or acyclic ketones in the presence of methanesulfonic acid leads directly to the benzofuran derivative via a proposed one-pot condensation-rearrangement-cyclisation reaction sequence in good to excellent yields.
see article for more examples
proposed mechanism
Key Words
benzofurans, hydroxylamines, sigmatropic rearrangement
ID: J60-Y2009-3300
