Synthesis 2017; 49(16): 3602-3608
DOI: 10.1055/s-0036-1588845
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Shicheng Shi
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA   Email: michal.szostak@rutgers.edu
,
Michal Szostak*
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA   Email: michal.szostak@rutgers.edu
› Author Affiliations
Further Information

Publication History

Received: 25 March 2017

Accepted after revision: 02 May 2017

Publication Date:
13 June 2017 (online)

Published as part of the Special Topic Advanced Strategies in Synthesis with Nickel

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.

Supporting Information

 
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