Nickel-Catalyzed sp³ C–H Bond Activation from Decarboxylative Cross­Coupling of α,β-Unsaturated Carboxylic Acids with Amides

Abstract

Nickel-catalyzed functionalization of C(sp³)–H bonds adjacent to a nitrogen atom in amides through decarboxylative cross-coupling of α,β-unsaturated carboxylic acids is reported. A possible reaction mechanism is proposed that involves radical intermediate species.

Key words

C–H bonds activation - nickel - cross-coupling - amides - radical reaction

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• 19 Typical Procedure: To a mixture of cinnamic acid (0.148 g, 1 mmol), Ni(OAc)₂·4H₂O (25 mg, 0.1 mmol), and N,N-dimethylacetamide (2 mL), tert-butyl hydroperoxide (0.39 g, 3 mmol, 70% in water) was added at r.t. dropwise. The resulting mixture was heated to 100 °C for 16 h, then the mixture was added to dichloromethane (40 mL) and washed with water and saturated brine. The organic solution was dried with anhydrous magnesium sulfate and the desired product was separated on a silica gel column (petroleum ether–EtOAc).