期刊
ORGANIC CHEMISTRY FRONTIERS
卷 5, 期 9, 页码 1527-1531出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8qo00219c
关键词
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资金
- Department of Science & Technology (DST-SERB), New Delhi, India [SB/FT/CS-117/2013]
- University Grant Commission (UGC), New Delhi
A novel, visible-light-mediated method for the construction of 2-substituted benzothiazoles from easily available thiophenols (2.0 equiv.) and alkyl/aryl nitriles (1.0 equiv.) in the presence of eosin Y (0.02 equiv.) under air atmosphere has been developed. The reaction proceeded smoothly, for a wide range of derivatives of thiophenols and nitriles, to give the expected products in moderate to good yields. A reaction mechanism involves the direct oxidative radical coupling of thiophenols with nitriles to afford iminyl radical intermediates giving the expected product by an intramolecular cyclization followed by hydrogen radical loss. To the best of our knowledge, this is the first example of the synthesis of 2-substituted benzothiazoles through sequential C-S and C-N bond formation reactions under photoredox catalysis.
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