Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 51, Pages 17878-17883Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b11942
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Funding
- The Scripps Research Institute (TSRI)
- Pfizer, Inc.
- Bristol-Myers Squibb
- National Science Foundation [CHE-1800280]
- NSF [NSF/DGE-1346837]
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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 method represents the first example of regiocon-trolled 1,2-diarylation directed by a native amide functional group. Computational analysis sheds light on the potential substrate binding mode and the role of the EDO ligand in the reductive elimination step.
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