Developing highly efficient catalytic protocols for C-sp(3)-H bond aerobic oxidation under mild conditions is a long-desired goal of chemists. Inspired by nature, a biomimetic approach for the aerobic oxidation of...

A visible-light-mediated late-stage arylation of N−S bonds in sulfonamides has been developed with using readily available imines as sulfonyl radical source. Diverse complex sulfones could be synthesized by prefunctionalizaiton and subsequent N−S bond arylation, demonstrating the advantages of using sulfonamides as sulfonylation reagents. Additionally, the mechanism research revealed that probably both EDA complex chemistry and photoredox catalysis were responsible for the formation of sulfones. This methodology characterized by broad substrate scope and simple reaction conditions also has high atom economy, since the aldehyde for the synthesis of imines could be recovered after workup of the reactions.

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Metal-free aerobic epoxidation of aliphatic alkenes, especially terminal alkenes, remains a significant challenge. Herein, a novel and practical synthetic method with Nhydroxyphthalimide (NHPI) as catalyst, isobutyraldehyde as sacrificial reductant and air as oxidant has been developed for the epoxidation of olefins in excellent to moderate conversions and selectivity at room temperature. Meanwhile, this synthetic methodology could efficiently convert inactive light olefins to corresponding epoxides which are highly desired in industry. Moreover, several free radicals in the reaction were identified and characterized by in situ electron paramagnetic resonance spectroscopy (in situ EPR) and highresolution mass spectrometry (HRMS). Mechanistic studies showed that the phthalimide N-oxyl radical (PINO•) generated from NHPI would promote the homolysis of isobutyraldehyde to carbonyl carbon radical by the extraction of hydrogen atoms.