Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration

Deprotonative directed ortho cupration of aromatic/heteroaromatic C–H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox...

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Published inJournal of the American Chemical Society Vol. 138; no. 29; pp. 9166 - 9171
Main Authors Tezuka, Noriyuki, Shimojo, Kohei, Hirano, Keiichi, Komagawa, Shinsuke, Yoshida, Kengo, Wang, Chao, Miyamoto, Kazunori, Saito, Tatsuo, Takita, Ryo, Uchiyama, Masanobu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.07.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
OXIDATION
METALATION
PALLADIUM-CATALYZED HYDROXYLATION
AMMONIA
MONOARYLATION
TERTIARY AMIDE
LITHIUM
ARYL CHLORIDES
TMP-ZINCATE
BOND-FORMATION
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Abstract Deprotonative directed ortho cupration of aromatic/heteroaromatic C–H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C–H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.
AbstractList Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.
Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I -> III -> I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.
Author Miyamoto, Kazunori
Hirano, Keiichi
Wang, Chao
Takita, Ryo
Yoshida, Kengo
Tezuka, Noriyuki
Uchiyama, Masanobu
Shimojo, Kohei
Saito, Tatsuo
Komagawa, Shinsuke
AuthorAffiliation RIKEN
Graduate School of Pharmaceutical Sciences
Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, and Elements Chemistry Laboratory
The University of Tokyo
AuthorAffiliation_xml – name: RIKEN
– name: The University of Tokyo
– name: Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, and Elements Chemistry Laboratory
– name: Graduate School of Pharmaceutical Sciences
Author_xml – sequence: 1
  givenname: Noriyuki
  surname: Tezuka
  fullname: Tezuka, Noriyuki
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  givenname: Kohei
  surname: Shimojo
  fullname: Shimojo, Kohei
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  givenname: Keiichi
  surname: Hirano
  fullname: Hirano, Keiichi
  email: k1hirano@mol.f.u-tokyo.ac.jp
– sequence: 4
  givenname: Shinsuke
  surname: Komagawa
  fullname: Komagawa, Shinsuke
– sequence: 5
  givenname: Kengo
  surname: Yoshida
  fullname: Yoshida, Kengo
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  givenname: Chao
  surname: Wang
  fullname: Wang, Chao
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  givenname: Masanobu
  surname: Uchiyama
  fullname: Uchiyama, Masanobu
  email: uchiyama@mol.f.u-tokyo.ac.jp
BackLink https://www.ncbi.nlm.nih.gov/pubmed/27348154$$D View this record in MEDLINE/PubMed
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Keywords OXIDATION
METALATION
PALLADIUM-CATALYZED HYDROXYLATION
AMMONIA
MONOARYLATION
TERTIARY AMIDE
LITHIUM
ARYL CHLORIDES
TMP-ZINCATE
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Snippet Deprotonative directed ortho cupration of aromatic/heteroaromatic C–H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high...
Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high...
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SubjectTerms Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration
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