Journal
ORGANIC LETTERS
Volume 20, Issue 4, Pages 930-933Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03783
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Funding
- Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions [16KJA150002]
- National Natural Science Foundation of China [21772137, 21672157, 21372174]
- project of scientific and technologic infrastructure of Suzhou [SZS201708]
- Ph.D. Programs Foundation of PAPD
- Soochow University
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A novel and efficient approach for the selenium functionalization of indoles was developed with selenium powder as the selenium source, catalyzed by 2,2,6,6-tetramethylpiperidinooxy (TEMPO) and employing O-2 as the green oxidant. This protocol provides a practical route for the synthesis of 3-selenylindole derivatives and has the advantages of readily available starting materials, mild reaction conditions, and a wide scope of substrates. Electron spin-resonance (ESR) studies reveal that the approach involves the formation of nitrogen-centered radicals and selenium radicals via oxidation of in situ generated selenoates.
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