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 Apr 2020 02:26
URI:	https://ueaeprints.uea.ac.uk/id/eprint/62046
DOI:	10.1002/chem.201201072

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