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

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.

Key words

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

• References


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