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Practical Intermolecular Hydroarylation of Terminal Alkenes via Reductive Heck Coupling

preprint
submitted on 20.06.2018 and posted on 20.06.2018 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.

Exports