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Selective Synthesis of Non‐Aromatic Five‐Membered Sulfur Heterocycles from Alkynes by using a Proton Acid/ N ‐Chlorophthalimide System
Author(s) -
Yu Wentao,
Zhu Baiyao,
Shi Fuxing,
Zhou Peiqi,
Wu Wanqing,
Jiang Huanfeng
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202010889
Subject(s) - sulfur , chemistry , proton , medicinal chemistry , combinatorial chemistry , organic chemistry , quantum mechanics , physics
A multicomponent strategy to achieve two different regioselectivities from alkynes, isothiocyanates and H 2 O with a proton acid/ N ‐chlorophthalimide (NCPI) system is described to selectively obtain non‐aromatic five‐membered sulfur heterocycles (1,3‐oxathiol‐2‐imines/thiazol‐2(3 H )‐one derivatives) through multiple bond formations. The process features readily available starting materials, mild reaction conditions, broad substrate scope, good functional‐group tolerance, high regio‐ and chemo‐ selectivities, gram‐scale synthesis and late‐stage modifications. Mechanistic studies support the proposal that the transformation process includes a combination of H 2 O and isothiocyanate, free‐radical formation, carbonation and intramolecular cyclization to give the products. Furthermore, the 1,3‐oxathiol‐2‐imine derivatives possess unique fluorescence characteristics and can be used as Pd 2+ sensors with a “turn‐off” response, demonstrating potential applications in environmental and biological fields.