Details

Autor(en) / Beteiligte

• Liu, Yu
• Sui, Jia-Li
• Yu, Wen-Qin
• Xiong, Bi-Quan
• Tang, Ke-Wen
• Zhong, Long-Jin

Titel

Visible-Light-Promoted Decarboxylative Alkylation/Cyclization of Vinylcycloalkanes

Ist Teil von

• Journal of organic chemistry, 2023-07, Vol.88 (13), p.8563-8575

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2023

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• An efficient strategy for visible-light-promoted decarboxylative alkylation of vinylcyclopropanes with alkyl N-(acyloxy)­phthalimide esters through the dual C–C bond and single N–O bond cleavage, employing triphenylphosphine and lithium iodide as the photoredox system to synthesize 2-alkylated 3,4-dihydronaphthalenes, has been established. This alkylation/cyclization involves a radical process and undergoes a sequence of N-(acyloxy)­phthalimide ester single-electron reduction, N–O bond cleavage, decarboxylative, alkyl radical addition, C–C bond cleavage, and intramolecular cyclization. Moreover, using the photocatalyst Na2-Eosin Y instead of triphenylphosphine and lithium iodide, the vinyl transfer products are acquired when vinylcyclobutanes or vinylcyclopentanes are utilized as alkyl radical receptors.