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Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization.

ABSTRACT: A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed ?-arylation reaction of an enolate, followed by in situ trapping with an electrophile, and aromatization with ammonium chloride. tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, 3-amino-4-alkyl isoquinolines were prepared in high yield.

SUBMITTER: Pilgrim BS

PROVIDER: S-EPMC3880054 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization.

Pilgrim Ben S BS Gatland Alice E AE McTernan Charlie T CT Procopiou Panayiotis A PA Donohoe Timothy J TJ

Organic letters 20131119 24

A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed α-arylation reaction of an enolate, followed by in situ trapping with an electrophile, and aromatization with ammonium chloride. tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, ...[more]

PMID: 24251885

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