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Nickel-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems

preprint
submitted on 03.03.2021, 06:39 and posted on 04.03.2021, 04:49 by Roman Kleinmans, Omar Apolinar, Joseph Derosa, Malkanthi Karunananda, Zi-Qi Li, Van Tran, Steven Wisniewski, Keary Engle

A conjunctive cross-coupling reaction of alkenyl ketones, aryl iodides, and arylboronic esters under nickel catalysis is reported. The reaction delivers the desired 1,2-diarylated products with moderate to excellent regiocontrol using a diverse array of ketone starting materials, as illustrated across over 40 examples. To showcase the versatility of this method, a representative product is diversified into a wide range of synthetically useful building blocks, that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis shows the effect of electronic factors on initial rates. To our knowledge, this method represents the first example of catalytic 1,2-diarylation of an alkene, directed by a native ketone functional group.

Funding

NSF-CHE-1800280

DAAD PROMOS Scholarship

NSF-DGE-1346837

NSF-DGE-1842471

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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