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Abstract Alkylamine structures represent one of the most functional and widely used in organic synthesis and drug design. However, the general methods for the functionalization of the shielded and deshielded alkyl radicals remain elusive. Here, we report a general deoxygenative amination protocol using alcohol-derived carbazates and nitrobenzene under electrochemical conditions. A range of primary, secondary, and tertiary alkylamines are obtained. This practical procedure can be scaled up through electrochemical continuous flow technique.

Electrochemical transformations use electrons and electron holes instead of chemical oxidants and reductants as reagents. Here, the authors report an electrochemical reductive deaminative cross-coupling of Katrizky salts with various radical acceptors, including examples of fluoroalkenylation, alkynylation and thiolation.

We present a versatile nickel-electrocatalytic deaminative cross-coupling platform for the efficient construction of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds from readily available alkyl bistriflimides. This methodology involves the assembly of two leaving groups on alkyl amines to form alkyl bistriflimides, followed by their effective coupling with a wide range of alkyl halides, alkyl pseudohalides, aryl halides, and alkenyl halides under electrochemical reductive conditions. Moreover, the successful application of electrochemical reductive relay cross-coupling and transition metal-free cross-electrophile coupling further demonstrates the versatility of alkyl bistriflimides as valuable building blocks in organic synthesis. Combined control experiments and density functional theory calculations provide insights into the reaction pathway and the crucial role of iodide in the catalytic process. [ABSTRACT FROM AUTHOR]