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Synthesis of Aziridines by Palladium‐Catalyzed Reactions of Allylamines with Aryl and Alkenyl Halides: Evidence of a syn ‐Carboamination Pathway
Author(s) -
Hayashi Sayuri,
Yorimitsu Hideki,
Oshima Koichiro
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200903178
Subject(s) - aziridine , aryl , palladium , halide , chemistry , intramolecular force , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry , ring (chemistry) , alkyl
Crazy rings : Treatment of N ‐arylallylamine with an aryl or alkenyl halide under palladium catalysis (see scheme; dba=dibenzylideneacetone, SPhos=2‐dicyclohexylphosphanyl‐2′,6′‐dimethoxybiphenyl) resulted in intramolecular cyclization to form the arylmethyl‐substituted aziridine with concomitant CC bond formation. The experiments for the elucidation of the reaction mechanism are also described.