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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Published inJournal 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
LanguageEnglish
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
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.8b05374