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Practical Intermolecular Hydroarylation of Terminal Alkenes via Reductive Heck Coupling

preprint
submitted on 20.06.2018, 09:11 and posted on 20.06.2018, 14:44 by John A. Gurak, Jr., Keary M. Engle
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.

Funding

1R35GM125052, NSF/DGE-1346837

History

Email Address of Submitting Author

keary@scripps.edu

Email Address(es) for Other Author(s)

jgurak@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

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