Hydrogenation of Quinaldine and Benzylic Aldehydes both Separately and Combined in a Tandem Hydrogenation–Reductive Alkylation of Quinaldine by Aldehydes with Iridium Benzoquinoline Catalysts

Autor:	Kerry C. Rippy, Graham E. Dobereiner, Laura J. Allen, Nilay Hazari, Jonathan Graeupner, Michael G. Manas, Robert H. Crabtree
Rok vydání:	2013
Předmět:	chemistry.chemical_classification Organic Chemistry Quinoline Quinaldine chemistry.chemical_element Alcohol Alkylation Aldehyde Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Cascade reaction Organic chemistry Iridium Physical and Theoretical Chemistry
Zdroj:	Organometallics. 32:4501-4506
ISSN:	1520-6041 0276-7333
Popis:	A series of cyclometalated benzoquinoline complexes of Ir(III) catalyze the hydrogenation of the heterocyclic ring of quinolines under mild conditions. Our best catalyst is active in a significantly wider range of solvents than our previous systems. In the presence of a suitable base, the Ir(III) species is also able to hydrogenate the C═O bonds of aldehydes. When quinolines and aldehydes are present together, the Ir(III) complex catalyzes a tandem reaction in which the quinoline is first hydrogenated to a tetrahydroquinoline that is subsequently reductively alkylated by the aldehyde. The reductive alkylation competes with the hydrogenation of the aldehyde to the alcohol, and therefore good yields of the alkylated tetrahydroquinoline require the presence of excess aldehyde.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f6a6b1bf825cd47cc9f23ab026fed3fa https://doi.org/10.1021/om400267n Zobrazit plný text záznamu