Transient Directing Group Strategy as a Unified Method for Site Selective Direct C4-H Halogenation of Indoles.

Autor: Kuang G; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.; College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China.; School of Laboratory Medicine, Hubei University of Chinese Medicine, Wuhan 430065, China., Liu D; School of Laboratory Medicine, Hubei University of Chinese Medicine, Wuhan 430065, China.; Chemistry and Environment Engineering College, Pingdingshan University, Pingdingshan 475000, China., Chen X; School of Laboratory Medicine, Hubei University of Chinese Medicine, Wuhan 430065, China., Liu G; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China., Fu Y; College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China., Peng Y; College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China., Li H; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China., Zhou Y; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2021 Nov 05; Vol. 23 (21), pp. 8402-8406. Date of Electronic Publication: 2021 Oct 19.
DOI: 10.1021/acs.orglett.1c03131
Abstrakt: A unified method for direct C4-H halogenation of indoles has been accomplished with the assistance of anthranilic acids as suitable transient directing groups. Exclusive site selectivity (one out of five potential reactive sites) as well as good functional group tolerance was obtained to install three kinds of halogen atoms (Cl, Br and I, respectively) by using inexpensive N -halosuccinimides (NXS) as halogen sources under mild conditions. Taking advantage of the rich functional groups in the product, a diversity of nitrogen-containing heterocycles were facily constructed via one-step late-stage derivations.
Databáze: MEDLINE