The role of the alcohol and carboxylic acid in directed ruthenium-catalyzed C(sp3)H α-alkylation of cyclic amines

Bergman, Sheba D., Storr, Thomas E., Prokopcová, Hana, Aelvoet, Karel, Diels, Gaston, Meerpoel, Lieven and Maes, Bert U. W. (2012) The role of the alcohol and carboxylic acid in directed ruthenium-catalyzed C(sp3)H α-alkylation of cyclic amines. Chemistry - A European Journal, 18 (33). pp. 10393-10398. ISSN 0947-6539

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Abstract

A general directed Ru-catalyzed C(sp3)[BOND]H α-alkylation protocol for piperidines (less-reactive substrates than the corresponding five-membered cyclic amines) has been developed. The use of a hindered alcohol (2,4-dimethyl-3-pentanol) as the solvent and catalyst activator, and a catalytic amount of trans-1,2-cyclohexanedicarboxylic acid is necessary to achieve a high conversion to product. This protocol was used to effectively synthesize a number of 2-hexyl- and 2,6-dihexyl piperidines, as well as the alkaloid (±)-solenopsin A. Kinetic studies have revealed that the carboxylic acid additive has a significant effect on catalyst initiation, catalyst longevity, and reverses the reaction selectivity compared with the acid-free reaction (promotes alkylation versus competing alkene reduction).

Item Type:	Article
Uncontrolled Keywords:	acid effects,c[bond]h activation,piperidines,ruthenium,selectivity
Faculty \ School:	Faculty of Science > School of Chemistry
Related URLs:	http://doi.wiley.com/10.1002/chem.201201...
Depositing User:	Pure Connector
Date Deposited:	13 Jan 2017 00:06
Last Modified:	22 Oct 2022 02:07
URI:	https://ueaeprints.uea.ac.uk/id/eprint/62046
DOI:	10.1002/chem.201201072

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