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A new radical relay approach for the efficient construction of alkylsulfonated indolo[2,1-a]isoquinoline-6(5H)-ones in moderate to good yields under mild conditions via SO2 insertion/Smiles rearrangement/intramolecular cyclization is developed. This approach utilizes 4-alkyl substituted Hantzsch esters as alkyl radical sources and further undergoes in situ SO2 insertion to obtain alkylsulfonyl radical species, which avoids the use of unstable alkyl sulfonyl chlorides and highly toxic sulfonyl hydrazides. Additionally, this method for the direct assembly of alkylsulfonated polycyclic molecule skeletons displays high chemical selectivity, broad substrate scope, and step-economy. [ABSTRACT FROM AUTHOR]

We here describe a new copper-catalyzed oxidative coupling of acids with alkanes for the selective synthesis of allylic esters and alkylalkenes. This method achieves multiple dehydrogenation and esterification, representing a new unactivated C(sp3)–H oxidative esterification of acids with common alkanes. [ABSTRACT FROM AUTHOR]