Visible-Light-Promoted Decarboxylative Alkylation/Cyclization of Vinylcycloalkanes

An efficient strategy for visible-light-promoted decarboxylativealkylation of vinylcyclopropanes with alkyl N-(acyloxy)phthalimideesters through the dual C-C bond and single N-O bondcleavage, employing triphenylphosphine and lithium iodide as the photoredoxsystem to synthesize 2-alkylated 3,4-dihydronaphthalenes, has beenestablished. This alkylation/cyclization involves a radical processand undergoes a sequence of N-(acyloxy)phthalimideester single-electron reduction, N-O bond cleavage, decarboxylative,alkyl radical addition, C-C bond cleavage, and intramolecularcyclization. Moreover, using the photocatalyst Na-2-EosinY instead of triphenylphosphine and lithium iodide, the vinyl transferproducts are acquired when vinylcyclobutanes or vinylcyclopentanesare utilized as alkyl radical receptors.

Automated summary

An efficient strategy for the visible-light-promoted decarboxylative alkylation of vinylcyclopropanes with alkyl N-(acyloxy)phthalimide esters has been developed using triphenylphosphine and lithium iodide as the photoredox system. This method involves the cleavage of dual C-C bonds and a single N-O bond and leads to the synthesis of 2-alkylated 3,4-dihydronaphthalenes. Additionally, when using Na-2-EosinY as the photocatalyst, the vinyl transfer products are obtained when vinylcyclobutanes or vinylcyclopentanes are utilized as alkyl radical receptors.