Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized -Heterocycles.

A convenient electrochemical oxidative cascade cyclization of alkenes equipped with pendant alcohols with general nucleophiles was developed. Using readily available diarylmethanimine and carboxylic acids as nucleophilic sources, a broad range of internal alkene and terminal alkene substrates could produce RCO- and ArCN-functionalized -heterocycles in moderate to high yields without the requirement for external oxidants and metals. These resulting products can subsequently be hydrolyzed to yield valuable NH- and OH-functionalized tetrahydrofurans and tetrahydropyranes under mild conditions.

Electrochemically Enabled Intramolecular Amino- and Oxysulfonylation of Alkenes with Sodium Sulfinates to Access Sulfonylated Saturated Heterocycles.

A practical and efficient electrochemical intramolecular amino- or oxysulfonylation of internal alkenes equipped with pendant nitrogen or oxygen-centered nucleophiles with sodium sulfinate was developed. Under undivided electrolytic cell conditions, a variety of sulfonylated -heterocycles and -heterocycles, such as tetrahydrofurans, tetrahydropyrans, oxepanes, tetrahydropyrroles, piperidines, δ-valerolactones, etc., were efficiently prepared from easily accessible unsaturated alcohols, carboxylic acids, and -tosyl amines without the need for additional metal or exogenous oxidant.

Complementary Copper-Catalyzed and Electrochemical Aminosulfonylation of -Homoallyl Benzimidates and -Alkenyl Amidines with Sodium Sulfinates.

A complementary copper-catalyzed and electrochemical aminosulfonylation of -homoallyl benzimidates and -alkenyl amidines with sodium sulfinates was developed. The terminal alkene substrate produced sulfone-containing 1,3-oxazines and tetrahydropyrimidines in the presence of Cu(OAc), AgCO, and DPP, and under similar reaction conditions, sulfonylated tetrahydro-1,3-oxazepines were prepared from 1-aryl-substituted -homoallyl benzimidates in moderate to good yields. For certain electron-rich 1,1-diaryl-substituted alkene substrates, the corresponding tetrahydro-1,3-oxazepines could also be obtained in similar or even higher yields via a green electrochemical technique.