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Directed Markovnikov Hydroarylation and Hydroalkenylation of Alkenes Under Nickel Catalysis

preprint
submitted on 24.05.2021, 17:47 and posted on 25.05.2021, 13:20 by Zi-Qi Li, Omar Apolinar, Ruohan Deng, Keary Engle
We report a full account of our research on nickel-catalyzed Markovnikov-selective hydroarylation and hydroalkenylation of non-conjugated alkenes, which has yielded a toolkit of methods that proceed under mild conditions with alkenyl sulfonamide, ketone, and amide substrates. Regioselectivity is controlled through catalyst coordination to the native Lewis basic functional groups contained within these substrates. To maximize product yield, reaction conditions were fine-tuned for each substrate class, reflecting the different coordination properties of the directing functionality. Detailed kinetic and computational studies shed light on the mechanism of this family of transformations, pointing to transmetalation as the turnover-limiting step.

Funding

NSF-CHE-1800280

NSF-DGE-1842471

History

Email Address of Submitting Author

keary@scripps.edu

Institution

The Scripps Research Institute

Country

United States

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.