A selenium-catalysed para-amination of phenols

Dingyuan Yan, Guoqiang Wang, Feng Xiong, Wei-Yin Sun, Zhuangzhi Shi, Yi Lu (), Shuhua Li () and Jing Zhao ()
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Dingyuan Yan: Nanjing University
Guoqiang Wang: Nanjing University
Feng Xiong: Nanjing University
Wei-Yin Sun: Nanjing University
Zhuangzhi Shi: Nanjing University
Yi Lu: Nanjing University
Shuhua Li: Nanjing University
Jing Zhao: Nanjing University

Nature Communications, 2018, vol. 9, issue 1, 1-9

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-catalysed para-amination of phenols while, in contrast, the reactions with sulfur donors are stoichiometric. A catalytic amount of phenylselenyl bromide smoothly converts N-aryloxyacetamides to N-acetyl p-aminophenols. When the para 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 the para-amination reaction by generating an AIEgen 2-(2′-hydroxyphenyl)benzothiazole (HBT) product in a fluorogenic fashion in a PBS buffer.

Date: 2018
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DOI: 10.1038/s41467-018-06763-4

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