Cp2Fe Mediated Electrochemical Synthesis of Phosphonylated Spirocyclic Indolines via Dearomatization of Indoles

Kangdong Mo; Xiaocong Zhou; Jian Wang; Ju Wu; Yufen Zhao

doi:10.1021/acs.orglett.3c01368

Cp₂Fe Mediated Electrochemical Synthesis of Phosphonylated Spirocyclic Indolines via Dearomatization of Indoles

Org Lett. 2023 Jun 2;25(21):3956-3960. doi: 10.1021/acs.orglett.3c01368. Epub 2023 May 18.

Authors

Kangdong Mo¹, Xiaocong Zhou¹, Jian Wang¹, Ju Wu¹, Yufen Zhao^{1

2}

Affiliations

¹ Institute of Drug Discovery Technology, Ningbo University, Zhejiang, 200433, China.
² Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, China.

PMID: 37199614
DOI: 10.1021/acs.orglett.3c01368

Abstract

A general and robust strategy for the synthesis of phosphonylated spirocyclic indolines has been developed through Cp₂Fe-catalyzed electrochemical dearomaztizaion of indoles, which has been proven challenging to achieve via chemical oxidants. A range of phosphonylated 3,3-spiroindolines were obtained in moderate to good yields with excellent diastereoselectivities. The synthetic application was further illustrated by its easy scalability and the antitumor activity of the product.