Practical Intermolecular Hydroarylation of Terminal Alkenes via Reductive Heck Coupling

20 June 2018, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 palladium-catalyzed 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. Deuterium-labeling 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.

Keywords

alkenes
Heck reaction
hydroarylation
palladium
regioselectivity

Supplementary materials

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