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A practical and straightforward access to pyrazolo[3,4-c]quinolines by molecular sieve mediated dehydrogenative [2 + 2 + 1] heteroannulation of N-(o-alkenylaryl)imines with aryldiazonium salts is described using a sp3-hybrid carbon atom as a one-carbon unit. The reaction enables the formation of three new chemical bonds, a C–C bond and two C–N bonds, in a single reaction and features simple operation and excellent functional group tolerance.

A new copper-catalyzed oxidative difunctionalization of enol ethers with α-amino carbonyl compounds and hydroperoxides is developed. This method is experimentally simple while allowing for regioselective access to 2-amino-3,4-dioxy carbonyl compounds in good yields, and represents the first example of alkene oxyalkylation through C(sp(3))-H functionalization.

A novel metal-free oxidative 1,2-alkylarylation of unactivated alkenes with the α-C(sp3)–H bonds of acetonitriles for the synthesis of 5-oxo-pentanenitriles is presented. In the presence of TBPB (tert-butyl peroxybenzoate), a variety of α-aryl allylic alcohols underwent the 1,2-alkylarylation reaction with acetonitriles, giving 5-oxo-pentanenitriles in good to excellent yields. This method proceeds via the C(sp3)–H oxidative coupling with the C–C double bond and 1,2-aryl-migration, and represents a new access to acyclic molecules through metal-free oxidative alkene 1,2-alkylarylation.

2,3-Epoxy ketones [(III) and (V)] are synthesized through an oxidative radical pathway with a broad substrate scope and excellent selectivity control.

Mono- and difunctionalization of a broad scope of non-activated alkenes is achieved with excellent chemoselectivities by a new oxidative coupling method.