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Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides

preprint
submitted on 07.11.2018 and posted on 07.11.2018 by Joseph Derosa, Roman Kleinmans, Van Tran, Malkanthi Karunananda, Steven Wisniewski, Martin Eastgate, Keary Engle
A nickel-catalyzed conjunctive cross-coupling of simple alkenyl amides with aryl iodides and aryl boronic esters is reported. The reaction is enabled by an electron-deficient olefin (EDO) ligand, dimethyl fumarate, and delivers the desired 1,2-diarylated products with excellent regiocontrol. Under optimized conditions, a wide range of amides derived from 3-butenoic acid, 4-pentenoic acid, and allyl amine are compatible substrates. This methodology represents the first example of regiocontrolled 1,2-diarylation directed by a native amide functional group. Computational analysis sheds light on potential substrate binding mode and the role of EDO ligand in the reductive elimination step.

Funding

NSF-CHE-1800280, NSF-DGE-1346837

History

Email Address of Submitting Author

keary@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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