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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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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Abstract 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.
AbstractList 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.
Author Cai, Chun
Bu, Mei-jie
Lu, Guo-ping
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  givenname: Guo-ping
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  givenname: Chun
  surname: Cai
  fullname: Cai, Chun
  email: c.cai@mail.njust.edu.cn
  organization: Nanjing Univ Sci & Technol, Chem Engn Coll, Nanjing 210094, Jiangsu, Peoples R China
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Issue 13
Keywords 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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Publisher Thieme Medical Publishers
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Snippet 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...
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StartPage 1841
SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Ascorbic Acid Promoted Metal-Free Synthesis of Aryl Sulfides with Anilines Nitrosated in Situ by tert-Butyl Nitrite
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