Nickel-Catalyzed Negishi Arylations of Propargylic Bromides: A Mechanistic Investigation

@inproceedings{Schley2014NickelCatalyzedNA,
  title={Nickel-Catalyzed
Negishi Arylations of Propargylic
Bromides: A Mechanistic Investigation},
  author={Nathan D Schley and Gregory C Fu},
  booktitle={Journal of the American Chemical Society},
  year={2014}
}
Although nickel-catalyzed stereoconvergent couplings of racemic alkyl electrophiles are emerging as a powerful tool in organic chemistry, to date there have been no systematic mechanistic studies of such processes. Herein, we examine the pathway for enantioselective Negishi arylations of secondary propargylic bromides, and we provide evidence for an unanticipated radical chain pathway wherein oxidative addition of the C-Br bond occurs through a bimetallic mechanism. In particular, we have… CONTINUE READING
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For leading references to mechanistic work on nickelcatalyzed crosscouplings of alkyl electrophiles , see : Hu

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