Electrochemical Oxidative Phosphorylations of Glycine Derivatives with R₂P(O)−H‐Containing Compounds via C(sp³)−H Functionalisation

Abstract

Herein, we report the development of transition‐metal‐catalyst‐ and external‐oxidant‐free electrochemical cross‐coupling hydrogen‐evolution chemistry involving glycine amides and diarylphosphine oxides. A broad range of biologically active α‐aminophosphonates was obtained in moderate to good yields in a clean and sustainable manner. Moreover, the TBAB (tetrabutylammonium bromide) electrolyte was recycled four times without obvious loss of reaction activity. Moreover, this protocol was performed on the gram scale under slightly modified electrolytic conditions or in combination with continuous flow microreactor technology. Control experiments were used to disclose a possible free‐radical mechanism.

Stabilized Carbon‐Centered Radical‐Mediated Carbosulfenylation of Styrenes: Modular Synthesis of Sulfur‐Containing Glycine and Peptide Derivatives

“…Notably, this system demonstrates compatibility with biomolecules and biotransformations. [32][33][34][35][36][37][38][39][40][41][42][43][44]…”

Phospha-Mannich reactions of phosphinous acids R 2 P–OH and their derivatives

“…P(O),NH-acetals, obtained by electrochemical reaction of N-aryl glycinamides with SPOs. [199] Figure S17. P(O),N-acetals, obtained by reaction of aryne precursors with formamides and SPOs.…”

Visible-Light-Induced Metal- and Photosensitizer-Free C(sp3)–H Phosphorylation of 3,4-Dihydroquinoxalin-2(1H)-ones with Diphenylphosphine Oxide

“…Only one example was obtained (Scheme a) . In addition, there have been significant advances in the techniques for constructing organic compounds containing phosphorus groups . To date, although visible-light-induced photoredox catalysis has been widely employed in the formation of C–P bonds, to the best of our knowledge the direct phosphonation of 3,4-dihydroquinoxalin-2(1 H )-one under visible-light-induced aerobic conditions at room temperature has not been attempted.…”