A Convenient Solid-Phase Synthesis of Coumarins by TMSOTf-Catalyzed Intramolecular Seleno-Arylation of Tethered Alkenes

TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno functionality, followed by syn elimination of selenoxides to provide coumarins in good yields and purities. Suzuki cross-coupling reaction of the resin-bound bromodihydrocoumarin was also performed, and biphenyl coumarin was obtained by subsequent cleavage of selenium linker.