Synthesis of Tetrahydrocarbazol-4-ones via Rh(III)-Catalyzed C-H Activation/Annulation of Arylhydrazines with Iodonium Ylides

He Li; Haichun Gu; Ye Lu; Ning Xu; Narenchaoketu Han; Jiaqi Li; Jinghai Liu; Jinglin Liu

doi:10.1021/acs.joc.2c00852

Synthesis of Tetrahydrocarbazol-4-ones via Rh(III)-Catalyzed C-H Activation/Annulation of Arylhydrazines with Iodonium Ylides

J Org Chem. 2022 Jun 17;87(12):8142-8150. doi: 10.1021/acs.joc.2c00852. Epub 2022 Jun 8.

Authors

He Li¹, Haichun Gu¹, Ye Lu^{1

2}, Ning Xu¹, Narenchaoketu Han³, Jiaqi Li¹, Jinghai Liu^{1

2}, Jinglin Liu^{1

4}

Affiliations

¹ College of Chemistry and Materials Science, Inner Mongolia Minzu University, Tongliao 028000, China.
² Inner Mongolia Key Laboratory of Carbon Nanomaterials, Nano Innovation Institute (NII), Inner Mongolia Minzu University, Tongliao 028000, China.
³ College of Traditional Mongolian Medicine, Inner Mongolia Minzu University, Tongliao 028000, China.
⁴ Inner Mongolia Key Laboratory for the Natural Products Chemistry and Functional Molecular Synthesis, Inner Mongolia Minzu University, Tongliao 028000, China.

PMID: 35675060
DOI: 10.1021/acs.joc.2c00852

Abstract

The rhodium(III)-catalyzed C-H activation followed by intramolecular annulation reactions between arylhydrazines and iodonium ylides under suitable conditions has been described. Tetrahydrocarbazol-4-ones are readily achieved with moderate to excellent yields. The synthetic protocol features a wide range of substrates with high functional group tolerance. The gram-scale reaction and derivatization of the product demonstrate the synthetic practicality and utilization of this method.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Rhodium* / chemistry

Substances

Rhodium