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Olefin Metathesis of Amine‐Containing Systems: Beyond the Current Consensus
Author(s) -
Compain Philippe
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700161
Subject(s) - chemistry , amine gas treating , steric effects , metathesis , salt metathesis reaction , catalysis , olefin metathesis , combinatorial chemistry , organic chemistry , olefin fiber , reactivity (psychology) , polymerization , medicine , alternative medicine , pathology , polymer
Olefin metathesis is one of the most powerful synthetic tool to access amine‐containing heterocycles and alkaloids. A major drawback associated with the use of amines concerns their ability to coordinate to metal‐alkylidene complexes and to interfere unproductively with catalytic activity. Based on literature precedents, it has been established as a “dogma” that efficient metathesis reactions are suppressed in the presence of basic amines and that such substrates must invariably be deactivated by conversion of the amines to the corresponding carbamates or ammonium salts. However, an increasing number of examples of amine‐containing compounds that are good substrates for metathesis is being reported in the literature. How can this “non‐classical” reactivity be rationalized and exploited? The purpose of this review is to provide an overview of successful metathesis reactions performed with amine‐containing compounds in order to allow some guidelines to be formulated. A special emphasis is placed on the different parameters that may influence the outcome of the reaction such as steric effects, amine basicity, and the nature of the catalyst.