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Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones

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journal contribution
posted on 12.06.2018 by Prakash Basnet, Roshan K. Dhungana, Surendra Thapa, Bijay Shrestha, Shekhar KC, Jeremiah M. Sears, Ramesh Giri
We disclose a [(PhO)3P]/NiBr2-catalyzed regioselective β,δ-diarylation of unactivated olefins in ketimines with aryl halides and arylzinc reagents. This diarylation proceeds at remote locations to the carbonyl group to afford, after simple H+ workup, diversely substituted β,δ-diarylketones that are otherwise difficult to access readily with existing methods. Deuterium-labeling and crossover experiments indicate that diarylation proceeds by ligand-enabled contraction of transient nickellacycles.