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First Metal- and Base-Free Selective Oxidative Coupling of Thiols in Neat Ionic Liquids: NMR Probed “Ambiphilic” Character of Neutral [hmim]Br towards Atom-Efficient Synthesis of Disulfides

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Title First Metal- and Base-Free Selective Oxidative Coupling of Thiols
in Neat Ionic Liquids: NMR Probed “Ambiphilic” Character of
Neutral [hmim]Br towards Atom-Efficient Synthesis of Disulfides
 
Creator Kumar, Rajesh
Sharma, Nandini
Sharma , U K
Shard , Amit
Sinha, Arun K
 
Subject Plant sciences
Natural Product Chemistry
 
Description The selective oxidative coupling of thiols
has been studied in several imidazolium-based ionic
liquids in the absence of any base/metal catalysts.
Disulfides were obtained from the corresponding
thiols in good to excellent yields in 1-hexyl-3-methylimidazolium
bromide ([hmim]Br). Furthermore,
a 1H NMR-based mechanistic study of the S–S
bond formation demonstrated the cooperative role
of halide anion and imidazolium cation of
[hmim]Br as an “ambiphile” – a character found to
be imperative for the efficient syntheses of disulfides.
The developed methodology is simple, selective
and green that utilises molecular oxygen as an
oxidant and produces water as the only by-product.
 
Date 2012
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://ihbt.csircentral.net/1290/1/68_First_Metal-_and_Base-Free_Selective%2C_2012.pdf
Kumar, Rajesh and Sharma, Nandini and Sharma , U K and Shard , Amit and Sinha, Arun K (2012) First Metal- and Base-Free Selective Oxidative Coupling of Thiols in Neat Ionic Liquids: NMR Probed “Ambiphilic” Character of Neutral [hmim]Br towards Atom-Efficient Synthesis of Disulfides. Journal of Advanced Synthesis & Catal., 354. pp. 2107-2112.
 
Relation http://ihbt.csircentral.net/1290/