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Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides.

ABSTRACT: A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.

SUBMITTER: Larionov OV

PROVIDER: S-EPMC4134923 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides.

Larionov Oleg V OV Stephens David D Mfuh Adelphe A Chavez Gabriel G

Organic letters 20140110 3

A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents. ...[more]

PMID: 24410049

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