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The (Porphyrin)ruthenium‐Catalyzed Aziridination of Olefins Using Aryl Azides as Nitrogen Sources
Author(s) -
Fantauzzi Simone,
Gallo Emma,
Caselli Alessandro,
Piangiolino Cristiana,
Ragaini Fabio,
Cenini Sergio
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700678
Subject(s) - chemistry , nitrene , ruthenium , amination , porphyrin , aryl , catalysis , steric effects , azide , reactivity (psychology) , organic chemistry , medicinal chemistry , combinatorial chemistry , medicine , alkyl , alternative medicine , pathology
Aryl azides have been used as atom‐efficient nitrene transfer reagents in the (porphyrin)ruthenium‐catalyzed amination of olefins. Several azides, olefins and [Ru(porphyrin)CO] complexes were tested to investigate the scope and limits of the reaction. Quantitative yields and short reaction times were achieved by using terminal olefins and aryl azides bearing electron‐withdrawing groups on the aryl moiety. The reactions were influenced by steric factors. Internally disubstituted olefins exhibited a lower reactivity and tri‐ and tetrasubstituted olefins did not react at all. A very high turnover number (TON) for the [Ru(TPP)CO] (TPP = tetraphenylporphyrin dianion) catalyzed amination of α‐methylstyrene by p ‐nitrophenyl azide was obtained.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)