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

FIGUEROA, R. N.; HEREDIA, ADRIAN A; ALICIA B. PEÑÉÑORY; SAMPEDRO, D. ; ARGÜELLO, JUAN E.; GABRIELA OKSDATH-MANSILLA

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; 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.