Work

I2-Photocatalyzed Cascade Reaction of 1-Isothiocyanatonaphthalenes with Amines to Give Naphtho[1,2- d ]thiazol-2-Amines

Year: 2026

Type: article

Abstract: Visible light initiates an I2-photocatalyzed cascade reaction of 1-isothiocyanatonaphthalenes and amines using O2 as the oxidant to N-substituted naphtho[1,2-d]thiazol-2-amines in good to excellent yields. This methodology is operationally simple, exhibits excellent functional group tolerance, and proceeds efficiently on a gram scale. The mechanism involves oxidation of the anion of in situ-formed N-(naphthalen-1-yl)carbothioamide by 1O2 photosensitized by *I2 or single-electron transfer from the excited charge-transfer complex between I2 and N-(naphthalen-1-yl)carbothioamide to give a sulfur radical that adds to the naphthalene ring, followed by rearomatization to give the product.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.6c01489

Authors: Da-Liang Zhu, Hao Wang, Qi Wu, David J. Young, Hong-Xi Li

Institutions: Soochow University, Yancheng Teachers University, University of Glasgow

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: Priority Academic Program Development of Jiangsu Higher Education Institutions

OpenAlex ID: W7212284283