Working Paper
Authors
- Joseph Derosa ,
- Roman Kleinmans ,
- Van Tran ,
- Malkanthi Karunananda ,
- Steven Wisniewski ,
- Martin Eastgate ,
- Keary Engle
The Scripps Research Institute
Abstract
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.
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Supporting Info
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