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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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
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Abstract	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.
AbstractList	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. 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. 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.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. O sub(2) in, H sub(2)O out: Various diamines and related bisnucleophiles readily undergo oxidative isocyanide insertion with Pd(OAc) sub(2) (1mol%) as the catalyst and O sub(2) as the terminal oxidant to give a diverse array of medicinally relevant Nheterocycles. The utility of this highly sustainable method is demonstrated by a formal synthesis of the antihistamines astemizole and norastemizole.
Author	Vlaar, Tjøstil Cioc, Razvan C. Mampuys, Pieter Orru, Romano V. A. Maes, Bert U. W. Ruijter, Eelco
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Copyright	Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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Notes	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
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Snippet	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... 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 sub(2) in, H sub(2)O out: Various diamines and related bisnucleophiles readily undergo oxidative isocyanide insertion with Pd(OAc) sub(2) (1mol%) as the...
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SubjectTerms	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
Title	Sustainable Synthesis of Diverse Privileged Heterocycles by Palladium-Catalyzed Aerobic Oxidative Isocyanide Insertion
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