Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)–C(sp3)/C(sp3)–C(sp2) Bond Formation and Mechanistic Studies

• Published in: Journal of the American Chemical Society Vol. 140; no. 31; pp. 9801 - 9805
• Main Authors: KC, Shekhar, Dhungana, Roshan K, Shrestha, Bijay, Thapa, Surendra, Khanal, Namrata, Basnet, Prakash, Lebrun, Robert W, Giri, Ramesh
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 08.08.2018; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; electron transfer; halogens; nickel; organic halogen compounds; Physical Sciences; regioselectivity; Science & Technology; ALKENYL CARBONYL-COMPOUNDS; ARYL GRIGNARD-REAGENTS; CROSS-COUPLING REACTIONS; TRANSIENT METALLACYCLES; ASYMMETRIC-SYNTHESIS; HECK REACTIONS; UNACTIVATED OLEFINS; TERMINAL ALKENES; ALKYL-HALIDES; INTERMOLECULAR CYANOTRIFLUOROMETHYLATION

We report a Ni-catalyzed regioselective alkylarylation of vinylarenes with alkyl halides and arylzinc reagents to generate 1,1-diarylalkanes. The reaction proceeds well with primary, secondary and tertiary alkyl halides, and electronically diverse arylzinc reagents. Mechanistic investigations by rad...