60805-64-3Relevant articles and documents
Spatial and temporal control of thiol-michael addition via photocaged superbase in photopatterning and two-stage polymer networks formation
Xi, Weixian,Peng, Haiyan,Aguirre-Soto, Alan,Kloxin, Christopher J.,Stansbury, Jeffery W.,Bowman, Christopher N.
, p. 6159 - 6165 (2014)
Photochemical processes enable spatial and temporal control of reactions, which can be implemented as an accurate external control approach in both polymer synthesis and materials applications. "Click" reactions have also been employed as efficient tools
CuI-catalyzed tandem synthesis of thioethers using aryl halides, electron-deficient alkenes, and sodium iso-propyl xanthogenate
Abbasi, Mohammad,Nowrouzi, Najmeh,Khezri, Rahimeh
, (2020/02/11)
A ligand-free, CuI-catalyzed protocol was developed for the one-step preparation of Michael adducts of aromatic thiols in high yields by reacting a mixture of an aryl halide and an electron-deficient alkene with sodium iso-propyl xanthogenate.
One-pot odorless thia-Michael reaction by copper ferrite nanoparticle-catalyzed reaction of elemental sulfur, aryl halides and electron-deficient alkenes
Gholinejad, Mohammad,Firouzabadi, Habib
, p. 5953 - 5959 (2015/08/06)
In this article we report a non-odorous protocol for the high yield formation of aryl-alkyl sulfides by the reaction of aryl iodides, bromides and boronic acids with elemental sulfur and electron-deficient alkenes, catalyzed by copper ferrite nanoparticles. The catalyst was easily separated using an external magnetic bar and recycled for subsequent runs, its catalytic activity being preserved.
Borontribromide-mediated C-C bond formation in cyclic ketones: A transition metal free approach
Ahmad, Imran,Pathak, Vinay,Vasudev, Prema G.,Maurya, Hardesh K.,Gupta, Atul
, p. 24619 - 24634 (2014/07/07)
Borontribromide (BBr3) is a well-known demethylating agent. The current investigation was focused on a new application of borontribromide as a C-C bond forming agent in cyclic ketones. In this study, borontribromide mediated C-C bond formation reactions of tetralones, chromenone, thiochromenone and indanones were explored. A methoxy group containing ketones showed selective C-C bond formation reaction instead of demethylation of the methoxy group. MM2 steric energy calculations for the final products showed that the reaction favored the formation of exo- or endo-cyclic double bond containing products, depending upon their low MM2 steric energy in a specific frame structure, as observed in X-ray crystallography. A comprehensive crystallographic and pi-stacking analysis of product 10a demonstrated the formation of 10a as an enantiomeric mixture, and its centre of inversion was stabilized by a set of three unique pi-pi interactions.
Neutral sulfur nucleophiles: Synthesis of thioethers and thioesters by substitution reactions of N-heterocyclic carbene boryl sulfides and thioamides
Pan, Xiangcheng,Curran, Dennis P.
supporting information, p. 2728 - 2731 (2014/06/09)
Newly discovered boryl sulfides and N-borylthioamides are shown to serve as neutral sources of sulfur nucleophiles in substitutions reactions. For example, heating of diMe-Imd-BH(SPh)2 with benzyl bromides, primary bromides, or acid chlorides provides the corresponding thioethers or thioesters in high yields. Likewise, N-phenyltetrazole thioethers/esters are made from a readily available N-borylthionotetrazole. The formation of the boryl sulfide and its onward nucleophilic substitution can be telescoped down to a one-pot reaction whose components are an NHC-borane (NHC-BH3), a disulfide, and an electrophile.
Organocatalytic asymmetric sulfa-michael addition of thiols to α,β-unsaturated hexafluoroisopropyl esters: Expeditious access to (R)-thiazesim
Fang, Xin,Li, Jun,Wang, Chun-Jiang
, p. 3448 - 3451 (2013/07/26)
A highly efficient organocatalytic asymmetric SMA reaction of hexafluoroisopropyl α,β-unsaturated esters has been developed. Introducing electron-withdrawing hexafluoroisopropyl ester is crucial to enhancing the electrophilicity of unsaturated esters as S
O-benzenedisulfonimide as a reusable brnsted acid catalyst for hetero-michael reactions
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
, p. 758 - 767 (2013/01/15)
The hetero-Michael reactions among various oxygen, sulfur, and nitrogen nucleophiles and ,-unsaturated compounds were carried out in the presence of catalytic amounts of o-benzenedisulfonimide as Brnsted acid organocatalyst. The reaction conditions were very mild, and the yields of target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. This ability grants economic and ecological advantages. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
Ecofriendly and efficient procedure for hetero-Michael addition reactions with an acidic ionic liquid as catalyst and reaction medium
Dabiri, Minoo,Salehi, Peyman,Bahramnejad, Mahboobeh,Baghbanzadeh, Mostafa
experimental part, p. 109 - 112 (2012/06/30)
1-Methylimidazolium trifluoroacetate ([Hmim]-TFA) is reported as a cost-effective catalyst for a simple and environmentally benign hetero-Michael reaction. [Hmim]TFA works both as reaction medium and catalyst. The reaction is applicable to various aromatic sulfur and nitrogen nucleophiles. This method has advantages such as high yields, short reaction time, and simple workup. The catalyst could be recycled several times without any loss of activity.
Reduction cleavage of S-S bond by Zn/Cp2tiCl2: Application for the synthesis of β-arylthiocarbonyl compounds
Xu, Xiao Bo,Yin, Xian Hong,Zhu, Yu Yang,Xu, Xin Hua,Luo, Tao,Li, Yin Hui,Lu, Xiong,Shao, Ling Ling,Pan, Jian Gao,Yang, Rong Hua
experimental part, p. 750 - 752 (2010/03/24)
Diaryl disulfides were reduced efficiently by a Zn/Cp2TiCl 2 system at room temperature in dry THF to give the corresponding nucleophilic sulfur anion-titanocene complex, followed by reaction with α, β-unsaturated esters (ketones or nitriles) to afford the corresponding β-arylthioesters(ketone or nitrile) in good yields.
Imidazolium-based polymer supported gadolinium triflate as a heterogeneous recyclable Lewis acid catalyst for Michael additions
Alleti, Ramesh,Oh, Woon Su,Perambuduru, Meher,Ramana,Prakash Reddy
, p. 3466 - 3470 (2008/09/21)
A heterogeneous Lewis acid catalytic system has been developed by incorporating gadolinium triflate on to poly[styrene-co-(1-((4-vinylphenyl)methyl)-3-methylimidazolium) tetrafluoroborate] (1-Gd(OTf)3), and the catalytic activity of this system has been examined for Michael additions of amines and thiols to α,β-unsaturated esters and acrylonitrile. The reactions proceed in moderate to excellent yields in the presence of catalytic system 1-Gd(OTf)3. The catalytic system could be efficiently recycled and reused.
