Electrochemical oxidative N–H/P–H cross-coupling with H₂ evolution towards the synthesis of tertiary phosphines

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...

Electrochemical Synthesis of β-Iodoesters by 1,2-Iodoesterization of Unactivated Alkenes with Carboxylic Acids and Tetrabutylammonium Iodide

“…On the basis of the previous works ,, and above control experimental results, a possible mechanism was proposed for the electrochemical oxidative radical iodination, bromination, and chlorination-difunctionalization of alkenes (Scheme ). Initially, the X – is likely to be first oxidized at the anode to generate Ẋ, which combines with alkene affording radical intermediate I .…”

Synthesis of N‐Sulfonyl Amidines and 1,3,4‐Oxadiazoles through Electrochemical Activation of DMF

“…Based on the evidence convened from the control experiments, cyclic voltammetry data and literature reports, the reaction mechanism of the transformations is proposed in Scheme 4. Two electron oxidations of iodide at the anodic surface generate I + , [25] which initiates the iodination of p-toluene sulfonamide (1 b) resulted TsNHI with more acidic NÀ H functionality. Strong hydrogen bonding between DMF and TsNHI and consequent proton transfer generates the ion pair B.…”

Electrochemical oxidative intramolecular annulation of aryl phosphine compounds: an efficient approach for synthesizing π-conjugated phosphonium salts

“…Organic electrochemical synthesis has been utilized to achieve the C-H activation/annulation, [22][23][24][25] the construction of polycyclic aza-fused arenes [26][27][28][29] and polycyclic S-containing arenes, 30 and the electrochemical transformation of phosphorus compounds have also been reported. [31][32][33] With our continuous interests in electrochemistry [34][35][36][37][38][39] and multiple C-H activations and annulation 19,40 , herein, we report a versatile electrochemical oxidative method under oxidant-free conditions to produce fused polycyclic phosphonium salts via the C-H activation/annulation of aryl phosphine compounds (Scheme 1d), and metals and oxidants could be readily avoided in this strategy.…”