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Direct beta -Alkylation of Aldehydes via Photoredox Organocatalysis

Direct beta -alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated beta -enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to pro... Full description

Journal Title: Journal of the American Chemical Society 20140422, Vol.136(19), pp.6858-6861
Main Author: Terrett, Jack
Other Authors: Clift, Michael , Macmillan, David
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0002-7863 ; E-ISSN: 1520-5126 ; DOI: 10.1021/ja502639e
Link: http://search.proquest.com/docview/1762062602/?pq-origsite=primo
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recordid: proquest1762062602
title: Direct beta -Alkylation of Aldehydes via Photoredox Organocatalysis
format: Article
creator:
  • Terrett, Jack
  • Clift, Michael
  • Macmillan, David
subjects:
  • Pathways
  • Spectroscopic Analysis
  • Activated
  • Spectroscopy
  • Aldehydes
  • Quenching
  • Radicals
  • Catalysis
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Journal of the American Chemical Society, 20140422, Vol.136(19), pp.6858-6861
description: Direct beta -alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated beta -enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce beta -alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C-H functionalization protocol can be achieved both inter- and intramolecularly. Mechanistic studies by various spectroscopic methods suggest that a reductive quenching pathway is operable.
language: eng
source:
identifier: ISSN: 0002-7863 ; E-ISSN: 1520-5126 ; DOI: 10.1021/ja502639e
fulltext: no_fulltext
issn:
  • 00027863
  • 0002-7863
  • 15205126
  • 1520-5126
url: Link


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subjectPathways ; Spectroscopic Analysis ; Activated ; Spectroscopy ; Aldehydes ; Quenching ; Radicals ; Catalysis ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionDirect beta -alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated beta -enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce beta -alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C-H functionalization protocol can be achieved both inter- and intramolecularly. Mechanistic studies by various spectroscopic methods suggest that a reductive quenching pathway is operable.
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abstractDirect beta -alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated beta -enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce beta -alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C-H functionalization protocol can be achieved both inter- and intramolecularly. Mechanistic studies by various spectroscopic methods suggest that a reductive quenching pathway is operable.
doi10.1021/ja502639e
urlhttp://search.proquest.com/docview/1762062602/
date2014-05-14