Photocatalytic Thio/Selenosulfonylation-Bicyclization of Indole-Tethered 1,6-Enynes Leading to Substituted Benzo[ c ]pyrrolo[1,2,3- lm ]carbazoles.

Autor: Zuo HD; Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.; School of Safety Science and Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. China., Chen X; Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.; School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, P. R. China., Zhang Y; Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.; School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, P. R. China., Liu JW; Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.; School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, P. R. China., Yan SH; Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.; School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, P. R. China., Li G; Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409, United States., Wang JY; Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.; School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 May 10; Vol. 26 (18), pp. 3828-3833. Date of Electronic Publication: 2024 Apr 29.
DOI: 10.1021/acs.orglett.4c00981
Abstrakt: The photocatalyzed radical-triggered thio/selenosulfonylation-bicyclization of indole-tethered 1,6-enynes has been established for the first time, enabling the synthesis of various previously unreported thio/selenosulfonylated benzo[ c ]pyrrolo[1,2,3- lm ]carbazoles with moderate to good yields under mild conditions. The reaction pathway was proposed, consisting of energy transfer, homolytic cleavage, radical addition, 5- exo - dig , radical coupling, and a Mallory reaction cascade. This approach exhibits a wide substrate compatibility and excellent tolerability toward various functional groups and is characterized by its remarkable efficiency in both bond formation and annulation.
Databáze: MEDLINE