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

A mild, metal-free synthesis of aryl sulfides has been disclosed. Aryl diazonium ion was generated by the in situ nitrosation of aniline, and it was reduced by ascorbic acid (vitamin C) to form aryl radical, which underwent a thiolation with disulfide to yield aryl sulfide. The reaction proceeded sm...

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Bibliographic Details
Published inSynlett Vol. 26; no. 13; pp. 1841 - 1846
Main Authors Bu, Mei-jie, Lu, Guo-ping, Cai, Chun
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 12.08.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM
ascorbic acid
ARENEDIAZONIUM SALTS
RADICAL ARYLATION
aryl sulfide
ONE-POT SYNTHESIS
NATURAL-PRODUCTS
radical reaction
C-S
SULFUR BOND FORMATION
metal-free
C(SP)-H BOND
carbon-sulfur bond formation
COUPLING REACTION
CHEMISTRY
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Summary:A mild, metal-free synthesis of aryl sulfides has been disclosed. Aryl diazonium ion was generated by the in situ nitrosation of aniline, and it was reduced by ascorbic acid (vitamin C) to form aryl radical, which underwent a thiolation with disulfide to yield aryl sulfide. The reaction proceeded smoothly without heating or irradiation. This strategy was also expanded to the synthesis of aryl selenides.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0034-1378738