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Ascorbic Acid Promoted Metal-Free Synthesis of Aryl Sulfides with Anilines Nitrosated in Situ by tert-Butyl Nitrite

Mei-jie Bu, Guo-ping Lu, Chun Cai*

*Chemical Engineering College, Nanjing University of Science & Technology, Nanjing, Jiangsu 210094, P. R. of China, Email:

M.-j. Bu, G.-p. Lu, C. Cai, Synlett, 2015, 26, 1841-1846.

DOI: 10.1055/s-0034-1378738

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In situ nitrosation of anilines followed by reduction with ascorbic acid to form aryl radicals and thiolation with disulfides provided aryl sulfides. This mild, metal-free synthesis of aryl sulfides proceeded smoothly without heating or irradiation. This strategy can be expanded to the synthesis of aryl selenides.

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Key Words

aryl sulfides, metal-free, ascorbic acid, tert-butyl nitrite, carbon-sulfur bond formation, radical reaction

ID: J60-Y2015