Ruthenium-Catalyzed Hydroxyl-Directed peri-Selective C-H Activation and Annulation of 1-Naphthols with CF3-Imidoyl Sulfoxonium Ylides for the Synthesis of 2-(Trifluoromethyl)-2,3-dihydrobenzo[ de]chromen-2-amines

Zuguang Yang; Jianhua Tang; Zhengkai Chen; Xiao-Feng Wu

doi:10.1021/acs.orglett.2c02685

Ruthenium-Catalyzed Hydroxyl-Directed peri-Selective C-H Activation and Annulation of 1-Naphthols with CF₃-Imidoyl Sulfoxonium Ylides for the Synthesis of 2-(Trifluoromethyl)-2,3-dihydrobenzo[ de]chromen-2-amines

Org Lett. 2022 Oct 14;24(40):7288-7293. doi: 10.1021/acs.orglett.2c02685. Epub 2022 Oct 4.

Authors

Zuguang Yang¹, Jianhua Tang¹, Zhengkai Chen¹, Xiao-Feng Wu^{2

3}

Affiliations

¹ Department of Chemistry, Key Laboratory of Surface and Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, China.
² Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning 116023, China.
³ Leibniz-Institut für Katalyse e. V., Albert-Einstein-Straβe 29a, 18059 Rostock, Germany.

PMID: 36194465
DOI: 10.1021/acs.orglett.2c02685

Abstract

A ruthenium-catalyzed peri-selective C-H activation and annulation of 1-naphthols with CF₃-substituted imidoyl sulfoxonium ylides that uses hydroxyl as a weakly coordinating directing group is disclosed. The strategy provides a facile and practical route to diverse trifluoromethyl-containing 2,3-dihydrobenzo[de]chromen-2-amines with high efficiency. Notable advantages of this protocol include readily available materials, excellent regioselectivity, good functional group compatibility, and scalability.