AI Article Synopsis
- The study demonstrates a new Ni-catalyzed method to selectively combine vinylarenes with alkyl halides and arylzinc compounds, resulting in the formation of 1,1-diarylalkanes.
- The reaction is effective with a variety of alkyl halides (primary, secondary, tertiary) and different types of arylzinc reagents.
- Mechanistic analysis suggests the process follows a catalytic cycle involving Ni in different oxidation states, with the key step being a rate-limiting single electron transfer that leads to halogen atom abstraction.
Article Abstract
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.
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| http://dx.doi.org/10.1021/jacs.8b05374 | DOI Listing |
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