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Practical Intermolecular Hydroarylation of Terminal Alkenes via Reductive Heck Coupling.

ABSTRACT: The hydroarylation of alkenes is an attractive approach to construct carbon-carbon (C-C) bonds from abundant and structurally diverse starting materials. Herein we report a palladiumcatalyzed reductive Heck hydroarylation of unactivated and heteroatom-substituted terminal alkenes with an array of (hetero)aryl iodides. The reaction is anti-Markovnikov selective and tolerates a wide variety of functional groups on both the alkene and (hetero)aryl coupling partners. Additionally, applications of this method to complex molecule diversifications were demonstrated. Deuteriumlabeling experiments are consistent with a mechanism in which the key alkylpalladium(II) intermediate is intercepted with formate and undergoes a decarboxylation/C-H reductive elimination cascade to afford the saturated product and turn over the cycle.

SUBMITTER: Gurak JA

PROVIDER: S-EPMC6207086 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Practical Intermolecular Hydroarylation of Terminal Alkenes via Reductive Heck Coupling.

Gurak John A JA Engle Keary M KM

ACS catalysis 20180824 10

The hydroarylation of alkenes is an attractive approach to construct carbon-carbon (C-C) bonds from abundant and structurally diverse starting materials. Herein we report a palladiumcatalyzed reductive Heck hydroarylation of unactivated and heteroatom-substituted terminal alkenes with an array of (hetero)aryl iodides. The reaction is anti-Markovnikov selective and tolerates a wide variety of functional groups on both the alkene and (hetero)aryl coupling partners. Additionally, applications of th ...[more]

PMID: 30393575

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