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The role of the alcohol and carboxylic acid in directed ruthenium-catalyzed C(sp3)-H -alkylation of cyclic amines
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| Abstract |
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| A general directed Ru-catalyzed C(sp3)?H a-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). |
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English
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Chemistry: a European journal. - Weinheim | |
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Weinheim : 2012
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0947-6539
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| Volume/pages |
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18:33(2012), p. 10393-10398
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| ISI |
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000307108100031
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