Electrochemical Synthesis and Reactivity of Three‐Membered Strained Carbo‐ and Heterocycles

Abstract

Three‐membered carbocyclic‐ and heterocyclic ring structures are versatile synthetic building blocks in organic synthesis owing to their biological importance. Also, the inherent strain of these three‐membered rings led to their ring‐opening functionalization via C‐C, C‐N, and C‐O bond cleavage. Traditional synthesis and ring‐opening methods of these molecules require the usage of acid catalysts or transition‐metals. Recently, electroorganic synthesis has emerged as a powerful tool for initiating new chemical transformations. In this review, the synthetic and mechanistic aspects of electro‐mediated synthesis and ring‐opening functionalization of three‐membered carbo‐ and heterocycles are highlighted.

Electrochemical Oxidative Dearomatization Strategy for Accessing Spiro[4.5]dienones and Derivatives

“…Utilizing this innate tool, C–C, C–O, and C–N bond formation and activation, rearrangement, and functionalization of the strained ring has been accomplished . Our group has also actively engaged in this field and has made several substantial contributions. − Interestingly, in 2019, Gao et al reviewed the significant advancements in electrochemical dearomatization . In 2022, Zhang and Lei et al explored the electrochemical oxidative dearomatization of anisole derivatives to synthesize spiropyrrolidines and spirolactones (Scheme A) .…”

Photochemical and Electrochemical Synthesis of Oxazoles and Isoxazoles: An Update

“…[13][14][15][16][17][18] Therefore, synthesis of these two crucial heterocyclic compounds using various green and sustainable methodologies has garnered significant enthusiasm within the community of synthetic organic chemists. [19] In this regard, photochemical [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] and electrochemical [38][39][40][41][42][43][44][45][46][47][48][49][50] techniques are considered as one of the most energy-efficient and environment-friendly approaches as they use photon or electron as activators and do not produce harmful waste. In recent years, extensive research has been done on photochemical and electrochemical synthesis of oxazoles.…”

Electrochemical Formation of Oxazolines by 1,3-Oxyfluorination of Non-activated Cyclopropanes

“…Several approaches have been used to achieve the ring cleavage of cyclopropanes, including the reactions of donor–acceptor cyclopropanes, , metal insertion, reaction with electrophiles and radical cations, and oxidation-induced activation . Activation by electrochemical oxidation is feasible for cyclopropane derivatives with lowered oxidation potential . Among them, anodic oxidation of arylcyclopropane 1 to a cation radical A has enabled transformations to access a range of the useful 1,3-difunctionalization reaction product 2 (Figure ).…”