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Multifunctionalization of alkenes via aerobic oxynitration and sp3 C-H oxidation.

A method for direct functionalization of three positions including an unactivated C-H bond of aliphatic alkenes using tert-butyl nitrite and molecular oxygen to give γ-lactols has been developed. The present reaction proceeds through a sequence of radical processes involving oxynitration followed by... Full description

Journal Title: Chemical communications (Cambridge England), March 18, 2013, Vol.49(22), pp.2198-2200
Main Author: Taniguchi, Tsuyoshi
Other Authors: Sugiura, Yuki , Hatta, Takashi , Yajima, Atsushi , Ishibashi, Hiroyuki
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1364-548X ; DOI: 1364-548X ; DOI: 10.1039/c3cc00130j
Link: http://search.proquest.com/docview/1289472444/?pq-origsite=primo
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title: Multifunctionalization of alkenes via aerobic oxynitration and sp3 C-H oxidation.
format: Article
creator:
  • Taniguchi, Tsuyoshi
  • Sugiura, Yuki
  • Hatta, Takashi
  • Yajima, Atsushi
  • Ishibashi, Hiroyuki
subjects:
  • Alkenes–Chemistry
  • Lactones–Chemical Synthesis
  • Molecular Structure–Chemistry
  • Nitrites–Chemistry
  • Oxidation-Reduction–Chemistry
  • Oxygen–Chemistry
  • Alkenes
  • Lactones
  • Nitrites
  • N-Butyl Nitrite
  • Oxygen
ispartof: Chemical communications (Cambridge, England), March 18, 2013, Vol.49(22), pp.2198-2200
description: A method for direct functionalization of three positions including an unactivated C-H bond of aliphatic alkenes using tert-butyl nitrite and molecular oxygen to give γ-lactols has been developed. The present reaction proceeds through a sequence of radical processes involving oxynitration followed by aerobic oxidation of an sp(3) C-H bond. This multifunctionalization reaction requires neither metallic reagents nor photolysis and proceeds under mild conditions.
language: eng
source:
identifier: E-ISSN: 1364-548X ; DOI: 1364-548X ; DOI: 10.1039/c3cc00130j
fulltext: fulltext
issn:
  • 1364548X
  • 1364-548X
url: Link


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titleMultifunctionalization of alkenes via aerobic oxynitration and sp3 C-H oxidation.
creatorTaniguchi, Tsuyoshi ; Sugiura, Yuki ; Hatta, Takashi ; Yajima, Atsushi ; Ishibashi, Hiroyuki
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subjectAlkenes–Chemistry ; Lactones–Chemical Synthesis ; Molecular Structure–Chemistry ; Nitrites–Chemistry ; Oxidation-Reduction–Chemistry ; Oxygen–Chemistry ; Alkenes ; Lactones ; Nitrites ; N-Butyl Nitrite ; Oxygen
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descriptionA method for direct functionalization of three positions including an unactivated C-H bond of aliphatic alkenes using tert-butyl nitrite and molecular oxygen to give γ-lactols has been developed. The present reaction proceeds through a sequence of radical processes involving oxynitration followed by aerobic oxidation of an sp(3) C-H bond. This multifunctionalization reaction requires neither metallic reagents nor photolysis and proceeds under mild conditions.
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titleMultifunctionalization of alkenes via aerobic oxynitration and sp3 C-H oxidation.
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