Pd-Promoted Cyclization of (Z)-Pent-2-en-4-yn-1-yl Alkanoates Leading to Furans via an Acyl Group Shift and Further Synthetic Transformation

Chiang, Ai-ChunAi-ChunChiangLiu, Yi-HungYi-HungLiuSHIE-MING PENGSHIUH-TZUNG LIU2022-12-212022-12-212022-10-211523-7060https://scholars.lib.ntu.edu.tw/handle/123456789/626703Palladium-promoted acyl migration was observed in the reaction of (Z)-pent-2-en-4-yn-1-yl alkanoates in the presence of DBU to yield 2-(alkanoylmethyl)furan derivatives (2) in high yields. Compounds 2 then underwent oxidative decarbonylation to afford 2-acylfurans with O2 as the oxidant under mild and metal-free conditions. The mechanistic pathway of the reaction involving an intramolecular cyclization and acyl group shift is discussed.enCLEAVAGEPd-Promoted Cyclization of (Z)-Pent-2-en-4-yn-1-yl Alkanoates Leading to Furans via an Acyl Group Shift and Further Synthetic Transformationjournal article10.1021/acs.orglett.2c03147362196702-s2.0-85140416776WOS:000869069000001https://api.elsevier.com/content/abstract/scopus_id/85140416776