Synthesis of Aza‐Heterocycles from Oximes by Amino‐Heck Reaction

Abstract
Oxidative addition of oximes to palladium(0) complexes generates alkylideneaminopalladium‘II’ species, which are utilized as key intermediates for carbon–nitrogen bond formation. Various aza‐heterocycles, such as pyrrole, pyridine, isoquinoline, spiroimine, and azaazulene, can be synthesized from O‐pentafluorobenzoyloximes having an olefinic moiety via an intramolecular Heck‐type reaction ‘amino‐Heck reaction’ by treatment with a catalytic amount of a Pd‘0’ complex. © 2002 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 2: 268–277, 2002: Published online in Wiley InterScience (www.interscience.wiley.com) DOI 10.1002/tcr.10030