Copper-Mediated and Palladium-Catalyzed Cross-Coupling of Indoles and N -Methylpyridinium Salts: A Practical Way to Prepare 3-(Pyridin-2-yl)indoles.

Autor: Tang J; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu, Sichuan 610064, P. R. China.; Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, P. R. China., Li S; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu, Sichuan 610064, P. R. China.; Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, P. R. China., Zhang J; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu, Sichuan 610064, P. R. China.; Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, P. R. China., Yan MX; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu, Sichuan 610064, P. R. China.; Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, P. R. China., Shi YL; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu, Sichuan 610064, P. R. China.; Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, P. R. China., Zheng XL; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu, Sichuan 610064, P. R. China.; Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, P. R. China., Yuan ML; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu, Sichuan 610064, P. R. China.; Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, P. R. China., Fu HY; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu, Sichuan 610064, P. R. China.; Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, P. R. China., Li RX; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu, Sichuan 610064, P. R. China.; Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, P. R. China., Chen H; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu, Sichuan 610064, P. R. China.; Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, P. R. China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Jul 21; Vol. 25 (28), pp. 5203-5208. Date of Electronic Publication: 2023 Jul 13.
DOI: 10.1021/acs.orglett.3c01624
Abstrakt: Herein, a Pd/Cu bimetallic-catalyzed direct C-H heteroarylation of pyridines via the traceless protecting group strategy is described. A series of N -methyl-activated pyridines and 1-methylindoles are coupled with high regioselectivity to produce the corresponding 3-(pyridin-2-yl)indoles in moderate to good yields, wherein related electron-rich heterocycles (e.g., indole, 1-methylpyrrole, benzofuran, benzo[ b ]thiophene) are also applicable. Streamlined operation, good functional group tolerance, and late-stage modifications make this twofold C-H activation protocol an attractive route for the synthesis of 3-(pyridin-2-yl)indole derivatives.
Databáze: MEDLINE