A Mild Synthesis of 2‑Substituted Benzothiazoles via Nickel-Catalyzed Intramolecular Oxidative C–H Functionalization

A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst, arylthioureas undergo intramolecular oxidative C–H bond functionalization, giving the desired 2-aminobenzothiazoles in good to excellent yields....

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Published inJournal of organic chemistry Vol. 85; no. 2; pp. 493 - 500
Main Authors Gao, Ming-Yuan, Li, Jing-Hang, Zhang, Shi-Bo, Chen, Li-Jun, Li, Yue-Sheng, Dong, Zhi-Bing
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.01.2020
Amer Chemical Soc
Subjects
carbon-hydrogen bond activation
catalysts
catalytic activity
chemical bonding
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
nickel
organic chemistry
organic compounds
Physical Sciences
Science & Technology
METAL-FREE SYNTHESIS
CASCADE REACTIONS
S BOND FORMATION
COUPLING REACTIONS
DERIVATIVES
2-AMINOBENZOTHIAZOLES
CYCLIZATION
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Summary:A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst, arylthioureas undergo intramolecular oxidative C–H bond functionalization, giving the desired 2-aminobenzothiazoles in good to excellent yields. This protocol features an inexpensive catalyst, low catalyst loading, mild reaction conditions, a short reaction time, and good to excellent yields, and it can be scaled up easily to a gram scale with almost no yields decreasing.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.9b02543