Radical Amination of C(sp3)–H Bonds Using N‑Hydroxyphthalimide and Dialkyl Azodicarboxylate

A direct conversion of C(sp3)–H bonds to C(sp3)–N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodi...

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Published inJournal of organic chemistry Vol. 77; no. 22; pp. 9959 - 9969
Main Authors Amaoka, Yuuki, Kamijo, Shin, Hoshikawa, Tamaki, Inoue, Masayuki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.11.2012
Amer Chemical Soc
Subjects
Aliphatic compounds
Alkanes - chemistry
Amination
Azo Compounds - chemistry
Catalysis
Chemistry
Chemistry, Organic
Exact sciences and technology
Free radicals chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrogen Bonding
Molecular Structure
Nitrogen - chemistry
Noncondensed benzenic compounds
Organic chemistry
Phthalimides - chemistry
Physical Sciences
Preparations and properties
Reactivity and mechanisms
Science & Technology
Stereoisomerism
OXIDATION
FUNCTIONALIZATION
BENZYLIC POSITIONS
ACTIVATION
INTERMOLECULAR AMINATION
HYDROCARBONS
HYPERVALENT SULFONYLIMINO-LAMBDA-BROMANE
C-H AMINATION
CATALYSTS
MOLECULAR-OXYGEN
Stoichiometry
Catalytic reaction
Nitroxyl
Acetylenic compound
Carbon-hydrogen bond
Chemoselectivity
Aliphatic compound
Chemical bond
Propargylic compound
Natural compound
Organic carbamate
Imide
Trapping
Amine
Amination
Functionalization
Benzylic compound
Organic free radical
Hydrazine
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Abstract A direct conversion of C(sp3)–H bonds to C(sp3)–N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts as a trapping agent of the resultant carbon radical to generate the hydrazine derivatives. This C–H amination proceeds in a highly chemoselective manner with a wide applicability to functionalize benzylic, propargylic, and aliphatic C–H bonds. Furthermore, the obtained hydrazine compounds were readily converted to the corresponding carbamates or amines. Hence, the present protocol for direct introduction of the nitrogen functionality serves as a powerful tool for efficient construction of nitrogen-substituted natural products and pharmaceuticals.
AbstractList A direct conversion of C(sp(3))-H bonds to C(sp(3))-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts as a trapping agent of the resultant carbon radical to generate the hydrazine derivatives. This C-H amination proceeds in a highly chemoselective manner with a wide applicability to functionalize benzylic, propargylic, and aliphatic C-H bonds. Furthermore, the obtained hydrazine compounds were readily converted to the corresponding carbamates or amines. Hence, the present protocol for direct introduction of the nitrogen functionality serves as a powerful tool for efficient construction of nitrogen-substituted natural products and pharmaceuticals.
A direct conversion of C(sp3)–H bonds to C(sp3)–N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts as a trapping agent of the resultant carbon radical to generate the hydrazine derivatives. This C–H amination proceeds in a highly chemoselective manner with a wide applicability to functionalize benzylic, propargylic, and aliphatic C–H bonds. Furthermore, the obtained hydrazine compounds were readily converted to the corresponding carbamates or amines. Hence, the present protocol for direct introduction of the nitrogen functionality serves as a powerful tool for efficient construction of nitrogen-substituted natural products and pharmaceuticals.
A direct conversion of C(sp(3))-H bonds to C(sp3)-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts as a trapping agent of the resultant carbon radical to generate the hydrazine derivatives. This C-H amination proceeds in a highly chemoselective manner with a wide applicability to functionalize benzylic, propargylic, and aliphatic C-H bonds. Furthermore, the obtained hydrazine compounds were readily converted to the corresponding carbamates or amines. Hence, the present protocol for direct introduction of the nitrogen functionality serves as a powerful tool for efficient construction of nitrogen-substituted natural products and pharmaceuticals.
Author Inoue, Masayuki
Hoshikawa, Tamaki
Kamijo, Shin
Amaoka, Yuuki
AuthorAffiliation The University of Tokyo
AuthorAffiliation_xml – name: The University of Tokyo
Author_xml – sequence: 1
  givenname: Yuuki
  surname: Amaoka
  fullname: Amaoka, Yuuki
– sequence: 2
  givenname: Shin
  surname: Kamijo
  fullname: Kamijo, Shin
– sequence: 3
  givenname: Tamaki
  surname: Hoshikawa
  fullname: Hoshikawa, Tamaki
– sequence: 4
  givenname: Masayuki
  surname: Inoue
  fullname: Inoue, Masayuki
  email: inoue@mol.f.u-tokyo.ac.jp
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https://www.ncbi.nlm.nih.gov/pubmed/23113810$$D View this record in MEDLINE/PubMed
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Issue 22
Keywords OXIDATION
FUNCTIONALIZATION
BENZYLIC POSITIONS
ACTIVATION
INTERMOLECULAR AMINATION
HYDROCARBONS
HYPERVALENT SULFONYLIMINO-LAMBDA-BROMANE
C-H AMINATION
CATALYSTS
MOLECULAR-OXYGEN
Stoichiometry
Catalytic reaction
Nitroxyl
Acetylenic compound
Carbon-hydrogen bond
Chemoselectivity
Aliphatic compound
Chemical bond
Propargylic compound
Natural compound
Organic carbamate
Imide
Trapping
Amine
Amination
Functionalization
Benzylic compound
Organic free radical
Hydrazine
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SSID ssj0000555
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Snippet A direct conversion of C(sp3)–H bonds to C(sp3)–N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl...
A direct conversion of C(sp(3))-H bonds to C(sp3)-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl...
A direct conversion of C(sp(3))-H bonds to C(sp(3))-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl...
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SubjectTerms Aliphatic compounds
Alkanes - chemistry
Amination
Azo Compounds - chemistry
Catalysis
Chemistry
Chemistry, Organic
Exact sciences and technology
Free radicals chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrogen Bonding
Molecular Structure
Nitrogen - chemistry
Noncondensed benzenic compounds
Organic chemistry
Phthalimides - chemistry
Physical Sciences
Preparations and properties
Reactivity and mechanisms
Science & Technology
Stereoisomerism
Title Radical Amination of C(sp3)–H Bonds Using N‑Hydroxyphthalimide and Dialkyl Azodicarboxylate
URI http://dx.doi.org/10.1021/jo301840e
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