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

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

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: washinton; Año: 2019 vol. 84 p. 3871 - 3880

0022-3263

Saccharin 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.