Electrochemical Oxidative N-H/P-H Cross-coupling With H 2 Evolution ...

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Abstract

Tertiary phosphines(iii) find widespread use in many aspects of synthetic organic chemistry. Herein, we developed a facile and novel electrochemical oxidative N-H/P-H cross-coupling method, leading to a series of expected tertiary phosphines(iii) under mild conditions with excellent yields. It is worth noting that this electrochemical protocol features very good reaction selectivity, where only a 1 : 1 ratio of amine and phosphine was required in the reaction. Moreover, this electrochemical protocol proved to be practical and scalable. Mechanistic insights suggested that the P radical was involved in this reaction.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1

Scheme 1. Important surrogates of P III …

Scheme 1. Important surrogates of P III groups. (A) P III ligands; (B) P III …

Scheme 1. Important surrogates of PIII groups. (A) PIII ligands; (B) PIII chelation-assisted C–H functionalization.
Scheme 2

Scheme 2. Gram-scale synthesis.

Scheme 2. Gram-scale synthesis.

Scheme 2. Gram-scale synthesis.
Fig. 1

Fig. 1. Electron paramagnetic resonance (EPR) spectra.

Fig. 1. Electron paramagnetic resonance (EPR) spectra.

Fig. 1. Electron paramagnetic resonance (EPR) spectra.
Scheme 3

Scheme 3. Control experiments.

Scheme 3. Control experiments.

Scheme 3. Control experiments.
Scheme 4

Scheme 4. Proposed mechanism.

Scheme 4. Proposed mechanism.

Scheme 4. Proposed mechanism.
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