Silver-Mediated Trifluoromethylation–Iodination of Arynes

An unprecedented silver-mediated vicinal trifluoromethylation–iodination of arynes that quickly introduces CF3 and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF3 has been revealed, and 2,2,6,6-tetramethylpiperidine pla...

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Published inJournal of the American Chemical Society Vol. 135; no. 8; pp. 2955 - 2958
Main Authors Zeng, Yuwen, Zhang, Laijun, Zhao, Yanchuan, Ni, Chuanfa, Zhao, Jingwei, Hu, Jinbo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.02.2013
Amer Chemical Soc
Subjects
aromatic compounds
chemical reactions
Chemistry
Chemistry, Multidisciplinary
Hydrocarbons, Fluorinated - chemistry
Iodine - chemistry
Methylation
Physical Sciences
Science & Technology
silver
Silver - chemistry
BORONIC ACIDS
LEWIS-BASES
SULFONIUM SALTS
ATE-COMPLEXES
CATALYZED TRIFLUOROMETHYLATION
R-F
ARYL
C-13 NMR
AROMATIC-COMPOUNDS
REDUCTIVE ELIMINATION
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Abstract An unprecedented silver-mediated vicinal trifluoromethylation–iodination of arynes that quickly introduces CF3 and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF3 has been revealed, and 2,2,6,6-tetramethylpiperidine plays an important role in this difunctionalization reaction.
AbstractList An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF3 and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF3 has been revealed, and 2,2,6,6-tetramethylpiperidine plays an important role in this difunctionalization reaction.
An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF(3) and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF(3) has been revealed, and 2,2,6,6-tetramethylpiperidine plays an important role in this difunctionalization reaction.
An unprecedented silver-mediated vicinal trifluoromethylation–iodination of arynes that quickly introduces CF₃ and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF₃ has been revealed, and 2,2,6,6-tetramethylpiperidine plays an important role in this difunctionalization reaction.
An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF(3) and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF(3) has been revealed, and 2,2,6,6-tetramethylpiperidine plays an important role in this difunctionalization reaction.An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF(3) and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF(3) has been revealed, and 2,2,6,6-tetramethylpiperidine plays an important role in this difunctionalization reaction.
Author Zhang, Laijun
Hu, Jinbo
Zeng, Yuwen
Ni, Chuanfa
Zhao, Yanchuan
Zhao, Jingwei
AuthorAffiliation Chinese Academy of Sciences
AuthorAffiliation_xml – name: Chinese Academy of Sciences
Author_xml – sequence: 1
  givenname: Yuwen
  surname: Zeng
  fullname: Zeng, Yuwen
– sequence: 2
  givenname: Laijun
  surname: Zhang
  fullname: Zhang, Laijun
– sequence: 3
  givenname: Yanchuan
  surname: Zhao
  fullname: Zhao, Yanchuan
– sequence: 4
  givenname: Chuanfa
  surname: Ni
  fullname: Ni, Chuanfa
– sequence: 5
  givenname: Jingwei
  surname: Zhao
  fullname: Zhao, Jingwei
– sequence: 6
  givenname: Jinbo
  surname: Hu
  fullname: Hu, Jinbo
  email: jinbohu@sioc.ac.cn
BackLink https://www.ncbi.nlm.nih.gov/pubmed/23398454$$D View this record in MEDLINE/PubMed
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Keywords BORONIC ACIDS
LEWIS-BASES
SULFONIUM SALTS
ATE-COMPLEXES
CATALYZED TRIFLUOROMETHYLATION
R-F
ARYL
C-13 NMR
AROMATIC-COMPOUNDS
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Snippet An unprecedented silver-mediated vicinal trifluoromethylation–iodination of arynes that quickly introduces CF3 and I groups onto aromatic rings in a single...
An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF3 and I groups onto aromatic rings in a single...
An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF(3) and I groups onto aromatic rings in a single...
An unprecedented silver-mediated vicinal trifluoromethylation–iodination of arynes that quickly introduces CF₃ and I groups onto aromatic rings in a single...
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StartPage 2955
SubjectTerms aromatic compounds
chemical reactions
Chemistry
Chemistry, Multidisciplinary
Hydrocarbons, Fluorinated - chemistry
Iodine - chemistry
Methylation
Physical Sciences
Science & Technology
silver
Silver - chemistry
Title Silver-Mediated Trifluoromethylation–Iodination of Arynes
URI http://dx.doi.org/10.1021/ja312711c
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Volume 135
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