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Reactions of Lithium Silylcuprates with Pyrazolium and Indazolium Salts
Author(s) -
GonzálezNogal Ana M.,
Calle Mariola,
Cuadrado Purificación
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.200700742
Subject(s) - chemistry , lithium (medication) , reagent , silylation , ring (chemistry) , nitrogen , medicinal chemistry , inorganic chemistry , organic chemistry , catalysis , medicine , endocrinology
Although pyrazolium salts have been shown to be unreactive toward lithium carbocuprates, these substrates were opened by lithium silylcuprate reagents to give versatile N ‐silylated β‐enaminoimines stabilized by coordination of the silyl group with both nitrogen atoms. In contrast, the behaviour of indazolium salts on treatment with the same reagents is more complex. Depending on the substitution patterns of the indazolium salts, the nature of the silylcuprate and even on the temperature, we obtained 3‐silylindazolines and other interesting products resulting either from the opening of the heterocyclic ring or from modification by its opening/closing.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)