Visible-Light-Induced, Catalyst-Free Monofluoromethyl Sulfonylation of Alkenes with Iodine(III) Reagent and DABSO.

Autor: Ye ZP; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Yang JS; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Yang SJ; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Guo M; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Yuan CP; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Ye YQ; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Chen HB; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.; Jiangxi Time Chemical Company, Ltd., Fuzhou 344800, P. R. China., Xiang HY; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Chen K; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Yang H; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Sep 29; Vol. 25 (38), pp. 7062-7066. Date of Electronic Publication: 2023 Sep 19.
DOI: 10.1021/acs.orglett.3c02766
Abstrakt: A visible-light-induced radical relay strategy to access heterocycles bearing a monofluoromethylsufonyl moiety is reported, with PhI(OCOCH 2 F) 2 as the CH 2 F radical precursor and DABSO as the SO 2 source. A range of oxindoles, containing a CH 2 FSO 2 CH 2 - group at the C3 position, were synthesized from N -arylacrylamides in up to 97% yields. The protocol features catalyst-free photochemical tandem, mild reaction conditions, broad functional group compatibility, and good to excellent yields.
Databáze: MEDLINE