CHIN-HUNG LAI2026-10-162026-10-162022-05-06Pure ID: 14972915Pure UUID: a3f30d18-948c-44c2-b595-a335adc338af10.1021/acs.joc.2c00204https://www.scopus.com/pages/publications/85128688090https://scholars.csmu.edu.tw/handle/123456789/23520Methylene and methyl tricyclic isoquinolinones were selectively prepared using a palladium(II)-catalyzed aerobic aza-Wacker reaction, followed by a base- and temperature-controlled Heck reaction catalyzed by palladium(0). Exo- to endo-double-bond migration in isoquinolinones was achieved with 93-99% yields by treatment of the Heck products with Cs2CO3 in dimethyl sulfoxide (DMSO) at 150 °C. A probable mechanism for Cs2CO3-promoted olefin isomerization was proposed and examined using D-isotope labeling experiments. Finally, yuanamide, a 13-methyl-8-oxoprotoberberine alkaloid, was synthesized using the palladium-catalyzed aza-Wacker/Heck/migration sequence.13enjournal article