Nickel-Catalyzed Negishi Cross-Coupling of N -Acylsuccinimides: Stable, Amide-Based, Twist-Controlled Acyl-Transfer Reagents via N-C Activation

Shicheng Shi, Michal Szostak

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

This paper reports a room temperature, nickel-catalyzed Negishi cross-coupling of N -acylsuccinimides with arylzinc reagents via selective N-C bond cleavage enabled by amide bond twist. The reaction proceeds using a commercially available, air-stable Ni(II) precatalyst in the absence of additives under exceedingly mild conditions. Of broad interest, this report introduces N -acylsuccinimides as stable, crystalline, electrophilic, cost-effective, benign, amide-based acyl transfer reagents via acyl metal intermediates. The reaction selectivity is governed by half-twist of the amide bond in N -acylsuccinimides, thus opening the door for applications in metal-catalyzed manifolds via redox-neutral reaction pathways tuneable by amide bond distortion.

Original languageEnglish (US)
Pages (from-to)3602-3608
Number of pages7
JournalSynthesis (Germany)
Volume49
Issue number16
DOIs
StatePublished - Aug 16 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Keywords

  • N-C activation
  • Negishi cross-coupling
  • acyl transfer
  • amide cross-coupling
  • nickel
  • succinimide
  • twisted amides

Fingerprint

Dive into the research topics of 'Nickel-Catalyzed Negishi Cross-Coupling of N -Acylsuccinimides: Stable, Amide-Based, Twist-Controlled Acyl-Transfer Reagents via N-C Activation'. Together they form a unique fingerprint.

Cite this