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Sustainable Synthesis of Diverse Privileged Heterocycles by Palladium‐Catalyzed Aerobic Oxidative Isocyanide Insertion
Author(s) -
Vlaar Tjøstil,
Cioc Razvan C.,
Mampuys Pieter,
Maes Bert U. W.,
Orru Romano V. A.,
Ruijter Eelco
Publication year - 2012
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.201207410
Subject(s) - isocyanide , oxidative phosphorylation , catalysis , palladium , chemistry , combinatorial chemistry , organic chemistry , biochemistry
O 2 in, H 2 O out : Various diamines and related bisnucleophiles readily undergo oxidative isocyanide insertion with Pd(OAc) 2 (1 mol %) as the catalyst and O 2 as the terminal oxidant to give a diverse array of medicinally relevant N heterocycles. The utility of this highly sustainable method is demonstrated by a formal synthesis of the antihistamines astemizole and norastemizole.