Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay

We describe a three-component carboacylation of alkenes via the merger of radical chemistry with nickel catalysis

Xian Zhao; Hai-Yong Tu; Lei Guo; Shengqing Zhu; Feng-Ling Qing; Lingling Chu

2018

Scholarcy highlights

  • The development of catalytic carboacylation of simple olefins, which would enable the rapid construction of ketones with high levels of complexity and diversity, is very challenging
  • The vast majority of alkene carboacylation reactions proceed via intramolecular insertion of an acyl-metal intermediate into an alkene
  • The development of fully intermolecular, three-component carboacylation of simple olefins, which would enable the rapid construction of ketone products with high levels of complexity and diversity, is highly desired and remains elusive
  • We envisioned that a radical relay strategy, involving radical addition to an alkene followed by alkyl radical capture by an acyl-nickel species would bypass the challenging acyl-metal/alkene capture required in a conventional two-electron mode
  • We have developed a robust strategy for intermolecular, three-component carboacylation of alkenes with acyl chlorides and fluoroalkyl iodides via a Ni-catalyzed radical relay
  • We expect that the generality of this methodology and readily availability of the starting materials will allow it to enjoy extensive application in the area of organic chemistry
  • After it was evacuated and backfilled nitrogen three times, CH3CN was added via a syringe, followed by the addition of acyl chloride

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