Regioselective Photocycloaddition of Saccharin Anion to π-Systems: Continuous-Flow Synthesis of Benzosultams

FIGUEROA, FRANCISCO N.; HEREDIA, ADRIÁN A.; PEÑÉÑORY, ALICIA B.; SAMPEDRO, DIEGO; ARGÜELLO, JUAN E.; OKSDATH-MANSILLA, GABRIELA

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: New York; Año: 2019 vol. 84 p. 3871 - 3871

0022-3263

accharin is a versatile scaffold to build up different heterocycles with relevance in asymmetric catalysis, agricultural chemistry, medicinal chemistry, and so forth. Here, we report a photochemical strategy to obtain seven-membered ring benzosultams in one step, using saccharin anion as starting material. The reaction can be improved in a photoflow reactor and its scope was evaluated. Furthermore, computational study at the CASPT2//CASSCF level of theory was also performed to rationalize the involved mechanism.