A selenium-catalysed para-amination of phenols. Issue 1 (December 2018)
- Record Type:
- Journal Article
- Title:
- A selenium-catalysed para-amination of phenols. Issue 1 (December 2018)
- Main Title:
- A selenium-catalysed para-amination of phenols
- Authors:
- Yan, Dingyuan
Wang, Guoqiang
Xiong, Feng
Sun, Wei-Yin
Shi, Zhuangzhi
Lu, Yi
Li, Shuhua
Zhao, Jing - Abstract:
- Abstract Antioxidant enzyme glutathione peroxidase (GPx) decomposes hydroperoxides by utilizing the different redox chemistry of the selenium and sulfur. Here, we report a Se-catalysedpara -amination of phenols while, in contrast, the reactions with sulfur donors are stoichiometric. A catalytic amount of phenylselenyl bromide smoothly convertsN -aryloxyacetamides toN -acetylp -aminophenols. When thepara position was substituted (for example, with tyrosine), the dearomatization 4, 4-disubstituted cyclodienone products were obtained. A combination of experimental and computational studies was conducted and suggested the weaker Se−N bond plays a key role in the completion of the catalytic cycle. Our method extends the selenium-catalysed processes to the functionalisation of aromatic compounds. Finally, we demonstrated the mild nature of thepara -amination reaction by generating an AIEgen 2-(2′-hydroxyphenyl)benzothiazole (HBT) product in a fluorogenic fashion in a PBS buffer. Selenium has emerged as a metalloid for the catalytic construction of C–N bonds; however no functionalisation of aromatic compounds has been developed yet. Here, the authors report thepara -amination of phenols via two successive sigmatropic rearrangements of a redox versatile Se–N bond.
- Is Part Of:
- Nature communications. Volume 9:Issue 1(2018)
- Journal:
- Nature communications
- Issue:
- Volume 9:Issue 1(2018)
- Issue Display:
- Volume 9, Issue 1 (2018)
- Year:
- 2018
- Volume:
- 9
- Issue:
- 1
- Issue Sort Value:
- 2018-0009-0001-0000
- Page Start:
- 1
- Page End:
- 9
- Publication Date:
- 2018-12
- Subjects:
- Biology -- Periodicals
Physical sciences -- Periodicals
505 - Journal URLs:
- http://www.nature.com/ncomms/index.html ↗
http://www.nature.com/ ↗ - DOI:
- 10.1038/s41467-018-06763-4 ↗
- Languages:
- English
- ISSNs:
- 2041-1723
- Deposit Type:
- Legaldeposit
- View Content:
- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library DSC - 6046.280270
British Library DSC - BLDSS-3PM
British Library HMNTS - ELD Digital store - Ingest File:
- 10818.xml