Nickel- and Rhodium-Catalyzed Addition of Terminal Silylacetylenes to Propargyl Amines: Catalyst-Dependent Complementary Regioselectivity

The cross-addition of terminal silylacetylenes to γ-arylated propargyl amines occurs efficiently via C−H cleavage by using either a nickel or rhodium catalyst. Taking advantage of the catalyst-controlled switching of regioselectivity in the reaction, both the 2- and 3-alkynylallylamines are readily...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-05, Vol.74 (9), p.3576-3578
Main Authors: Matsuyama, Naoto, Hirano, Koji, Satoh, Tetsuya, Miura, Masahiro
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:The cross-addition of terminal silylacetylenes to γ-arylated propargyl amines occurs efficiently via C−H cleavage by using either a nickel or rhodium catalyst. Taking advantage of the catalyst-controlled switching of regioselectivity in the reaction, both the 2- and 3-alkynylallylamines are readily accessible from the same starting materials.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900474d