A Direct C-H/Ar-H Coupling Approach to Oxindoles, Thio-oxindoles, 3,4-Dihydro-1H-quinolin-2-ones, and 1,2,3,4-Tetrahydroquinolines

A copper(II)-catalysed approach to oxindoles, thio-oxindoles, 3,4-dihydro-1H-quinolin-2-ones, and 1,2,3,4-tetrahydroquinolines via formal C-H, Ar-H coupling is described. In a new variant, copper(II) 2-ethylhexanoate has been identified as an inexpensive and efficient catalyst for this transformatio...

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Bibliographic Details
Published inChemistry : a European journal Vol. 20; no. 43; pp. 14063 - 14073
Main Authors Hurst, Timothy E., Gorman, Ryan M., Drouhin, Pauline, Perry, Alexis, Taylor, Richard J. K.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.10.2014
Wiley Subscription Services, Inc
Subjects
Atmospherics
Catalysts
Chemistry
Chemistry, Multidisciplinary
Copper
Copper compounds
Coupling
Joining
Moisture
Oxidants
Oxidizing agents
Physical Sciences
Precursors
Science & Technology
Synthesis
Transformations
ROOM-TEMPERATURE
3,3-DISUBSTITUTED OXINDOLES
ONE-POT
1,3-DICARBONYL COMPOUNDS
dihydroquinolinones
catalysis
RADICAL CYCLIZATION REACTIONS
ARYL C(SP)-H BONDS
oxindoles
METAL-FREE SYNTHESIS
tetrahydroquinolines
ACTIVATED ALKENES
INTRAMOLECULAR ALPHA-ARYLATION
LIGHT PHOTOREDOX CATALYSIS
copper
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Summary:A copper(II)-catalysed approach to oxindoles, thio-oxindoles, 3,4-dihydro-1H-quinolin-2-ones, and 1,2,3,4-tetrahydroquinolines via formal C-H, Ar-H coupling is described. In a new variant, copper(II) 2-ethylhexanoate has been identified as an inexpensive and efficient catalyst for this transformation, which utilises atmospheric oxygen as the re-oxidant.
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ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201403917