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An Efficient [2+3] Cycloaddition Approach to the Synthesis of Pyridyl‐Appended Fullerene Ligands
Author(s) -
Troshin Pavel A.,
Peregudov Alexander S.,
Mühlbacher David,
Lyubovskaya Rimma N.
Publication year - 2005
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.200500048
Subject(s) - chemistry , cycloaddition , fullerene , reagent , reactivity (psychology) , combinatorial chemistry , catalysis , transition metal , covalent bond , organic chemistry , medicine , alternative medicine , pathology
We have used 2‐, 3‐, and 4‐picolylamines and their various N ‐substituted derivatives as substrates to generate azomethine ylides for [2+3] cycloaddition to [60]fullerene. A considerable difference in the reactivity of isomeric picolylamines was observed; however, even less reactive 3‐picolylamines afford high yields of products under acid or base catalysis. This method provides easy access to a large family of valuable ligands (pyridyl‐substituted pyrrolidinofullerenes) that can be used in the design of transition‐metal complexes and non‐covalently bonded dyads with metalloporphyrins. Unusually high yields of products and convenience of synthetic procedures (2–10 min heating the reagents at reflux in 1,2‐dichlorobenzene in air in most cases) as well as a wide synthetic potential make this reaction a good alternative to the commonly used Prato method. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)