Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 32, Pages 12541-12544Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b07948
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Funding
- MEXT (Japan) [18H04253, 17KT0006, 15H05845, 15H03809]
- Grants-in-Aid for Scientific Research [15H03809, 18H04253, 17KT0006, 15H05845] Funding Source: KAKEN
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The nickel-catalyzed formal [5+2] cycloaddition of five-membered benzothiophenes and alkynes giving seven-membered benzothiepines via unprecedented dearomatization is reported. The reaction involves the carbothiolation of alkynes with sulfur-containing aromatic heterocycles affording sulfur-containing heterocyclic compounds via ring expansion. As a result, this method facilitates divergent access to thermally metastable benzothiepines. The structure of the thianickelacycle intermediate, which is formed via oxidative addition of the C-S bond in benzothiophenes to nickel(0), was confirmed by in situ X-ray absorption fine structure spectroscopy and density functional theory calculation.
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