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Synthesis of Aza‐Heterocycles from Oximes by Amino‐Heck Reaction
Author(s) -
Kitamura Mitsuru,
Narasaka Koichi
Publication year - 2002
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.10030
Subject(s) - heck reaction , chemistry , isoquinoline , pyrrole , intramolecular force , moiety , palladium , catalysis , pyridine , oxime , organic chemistry , medicinal chemistry
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