期刊
SYNLETT
卷 32, 期 19, 页码 1948-1952出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610785
关键词
nickel catalysis; cycloaddition; desulfidation; alkynes; benzothiazoles; trifluoromethylquinolines
资金
- Ministry of Education, Culture, Sports, Science and Technology (Japan) [20H02737, 18H04253, 17KT0006]
- [17KT06]
- Grants-in-Aid for Scientific Research [20H02737] Funding Source: KAKEN
A new nickel-catalyzed insertion reaction has been developed, where an alkyne is inserted into a 2-(trifluoromethyl)-1,3-benzothiazole to yield a novel compound. The structure of the intermediate was confirmed through X-ray single-crystal structure analysis and in situ X-ray absorption fine-structure spectroscopy.
We have developed a nickel-catalyzed insertion reaction of an alkyne into a 2-(trifluoromethyl)-1,3-benzothiazole to give a seven-membered benzothiazepine that is converted into a 2-(trifluoromethyl)quinoline by thermal desulfidation. This process can be considered a formal substitution of a sulfur atom with an alkyne. The structure of the thianickelacycle intermediate formed through oxidative addition of a C-S bond in the benzothiazole to nickel(0) was confirmed by X-ray single-crystal structure analysis and in situ X-ray absorption fine-structure spectroscopy.
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