Sustainable Synthesis of Diverse Privileged Heterocycles by Palladium-Catalyzed Aerobic Oxidative Isocyanide Insertion

O2 in, H2O out: Various diamines and related bisnucleophiles readily undergo oxidative isocyanide insertion with Pd(OAc)2 (1 mol %) as the catalyst and O2 as the terminal oxidant to give a diverse array of medicinally relevant N heterocycles. The utility of this highly sustainable method is demonstr...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 51; no. 52; pp. 13058 - 13061
Main Authors: Vlaar, Tjøstil, Cioc, Razvan C., Mampuys, Pieter, Maes, Bert U. W., Orru, Romano V. A., Ruijter, Eelco
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 21.12.2012
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
Antihistamines
Arrays
Astemizole - chemical synthesis
Astemizole - chemistry
Benzimidazoles - chemical synthesis
Benzimidazoles - chemistry
Catalysis
Cyanides - chemistry
Diamines
Diamines - chemistry
guanidines
Guanidines - chemistry
heterocycles
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
homogeneous catalysis
Insertion
isocyanides
Oxidants
oxidation
Oxidation-Reduction
Oxidizing agents
Palladium
Palladium - chemistry
Piperidines - chemical synthesis
Piperidines - chemistry
Synthesis
Terminals
Utilities
ISSN:1433-7851, 1521-3773, 1521-3773
Online Access:Get full text
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Summary:O2 in, H2O out: Various diamines and related bisnucleophiles readily undergo oxidative isocyanide insertion with Pd(OAc)2 (1 mol %) as the catalyst and O2 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.
Bibliography:ark:/67375/WNG-RDV0Z1G0-0
This work was financially supported by The Netherlands Organization for Scientific Research (NWO) by means of a TOP grant to R.V.A.O, and by the Hercules Foundation. We thank Elwin Janssen for technical assistance, Sanne Bouwman for HRMS measurements, and Dr. Andreas W. Ehlers for NMR spectroscopic measurements.
ArticleID:ANIE201207410
Netherlands Organization for Scientific Research (NWO)
istex:3939E6BD6F93A76CFF3AF2B7414B0E5C0648D5B8
Hercules Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
content type line 23
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201207410