Sodium Sulfite-Involved Photocatalytic Radical Cascade Cyclization of 2-Isocyanoaryl Thioethers: Access to 2-CF2/CF3-Containing Benzothiazoles

Yao Yuan; Wuheng Dong; Xiaoshuang Gao; Xiaomin Xie; Zhaoguo Zhang

doi:10.1021/acs.orglett.8b03710

Sodium Sulfite-Involved Photocatalytic Radical Cascade Cyclization of 2-Isocyanoaryl Thioethers: Access to 2-CF₂/CF₃-Containing Benzothiazoles

Org Lett. 2019 Jan 18;21(2):469-472. doi: 10.1021/acs.orglett.8b03710. Epub 2018 Dec 27.

Authors

Yao Yuan¹, Wuheng Dong¹, Xiaoshuang Gao¹, Xiaomin Xie¹, Zhaoguo Zhang^{1

2}

Affiliations

¹ Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering , Shanghai Jiao Tong University , 800 Dongchuan Road , Shanghai 200240 , China.
² State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.

PMID: 30588818
DOI: 10.1021/acs.orglett.8b03710

Abstract

A visible-light-induced radical cascade cyclization of 2-isocyanoaryl thioethers for the synthesis of 2-CF₂/CF₃-containing benzothiazoles has been developed. Sodium sulfite can participate in the photocatalytic cycle as a reductant that efficiently transforms Ir⁴⁺ into Ir³⁺ to promote the fluoroalkylation under mild reaction conditions.

Publication types

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