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

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

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...

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Veröffentlicht in:Journal of the American Chemical Society 2018-08, Vol.140 (31), p.9801-9805
Hauptverfasser: KC, Shekhar, Dhungana, Roshan K, Shrestha, Bijay, Thapa, Surendra, Khanal, Namrata, Basnet, Prakash, Lebrun, Robert W, Giri, Ramesh
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container_end_page 9805
container_issue 31
container_start_page 9801
container_title Journal of the American Chemical Society
container_volume 140
creator KC, Shekhar
Dhungana, Roshan K
Shrestha, Bijay
Thapa, Surendra
Khanal, Namrata
Basnet, Prakash
Lebrun, Robert W
Giri, Ramesh
description 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 radical probes, competition studies and quantitative kinetics reveal that the current reaction proceeds via a Ni(0)/Ni­(I)/Ni­(II) catalytic cycle by a rate-limiting direct halogen atom abstraction via single electron transfer to alkyl halides by a Ni(0)-catalyst.
doi_str_mv 10.1021/jacs.8b05374
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title Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)–C(sp3)/C(sp3)–C(sp2) Bond Formation and Mechanistic Studies
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