Sunlight Induced and Alternative Sc(OTf)3 Catalyzed Remote C−H Halogenation of Indoles

Author:

Liu Shanshan1ORCID,Zhou Xianying1,Jiao Lin‐Yu2,Li Chao13,Wang Zheng1

Affiliation:

1. Shaanxi Key Laboratory of Chemical Additives for Industry College of Chemistry and Chemical Engineering Shaanxi University of Science and Technology Xi'an Shaanxi 710021 P. R. China

2. School of Chemical Engineering Northwest University Xi'an Shaanxi 710069 P. R. China

3. Shaanxi Institute of Product Quality Supervision and Inspection Xi'an Shaanxi 710048 P. R. China

Abstract

AbstractA mild and catalyst‐free sunlight induced protocol for the remote meta bromination of electron‐deficient indoles is described for the first time. Herein, N‐bromosaccharin is activated by sunlight irradiation. Alternately, a synergistic activation model (Sc(OTf)3/HFIP) has also been developed for the activation of haloniums, complementary to the light induced strategy. In addition, the cascade C6‐H bromination and benzylic C−H oxidation under photocatalytic conditions was also discussed. High regio‐and chem‐selectivity, mild reaction conditions, and scalability demonstrate great potential of the developed methods in practical applications and further functionalization.

Funder

National Natural Science Foundation of China

Cyrus Tang Foundation

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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