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This study presents a novel approach for synthesizing benzo[ f ]isoindole dimers, which involves cascade cyclization and oxidative radical dimerization. Our method allows for the formation of up to five carbon-carbon bonds in a single reaction, exhibiting remarkable diastereoselectivity and regioselectivity. The mechanism and regioselectivity were investigated through a combination of experiments and calculations.

A general oxyalkylation of terminal alkynes enabled by iron catalysis has been developed. Primary and secondary alkyl iodides acted as the alkylating reagents and afforded a range of α-alkylated ketones under mild reaction conditions. Acetyl tert-butyl peroxide (TBPA) was used as the radical relay precursor, providing the initiated methyl radical to start the radical relay process. Preliminary mechanistic studies were conducted, and late-stage functionalizations of natural product derivatives were performed.

An environmentally benign, copper-catalyzed diazidation of a broad range of olefins, including vinylarenes, unactivated alkenes, allene, and dienes, under mild conditions with TMSN 3 (trimethylazidosilane) as azido source, has been developed. This reaction can be carried out in organic solvent or in aqueous solution where water is the sole solvent. The functional group compatibility of this reaction is good, which is proved by late-stage functionalizations of complex substrates.