23246-22-2

Upstream product

• 4779-86-6 sodium 1-buthanethiolate 
• 292638-85-8 acrylic acid methyl ester 
• 67-56-1 methanol 
• 22002-73-9 3-(butylthio)propionic acid 
• 109-79-5 n-butanethiol 
• 4269-98-1 butanethiol thiouronium hydrobromide 
• 100-46-9 benzylamine 

Relevant academic research and scientific papers

Zinc-catalyzed regioselective addition of alkyl thiols to alkenes via anion or radical reactions

Zn-catalyzed reactions of alkenes with alkyl thiols could afford alkyl sulfides regioselectively. When the ZnI2- catalyzed hydrothiolation of alkenes was achieved using alkyl thiols at 100 °C, Markovnikov-type alkyl sulfides were obtained in excellent yields without the formation of linear products. To the contrary, Zn(OAc)2- catalyzed reaction gave rise only to anti-Markovnikov-type products regioselectively. The reaction proceeded via a radical process.

Transition Metal-Free C-H Thiolation via Sulfonium Salts Using β-Sulfinylesters as the Sulfur Source

We disclose a direct C(sp)-, C(sp2)-, and C(sp3)-H thiolation reaction using β-sulfinylesters as the versatile sulfur source. The key step of this protocol is chemoselective C-S bond cleavage of the sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters. The successful capture of the acrylate byproduct supports a retro-Michael reaction mechanism.

Novel atom-economic reaction: Comprehensive utilization of S-alkylisothiouronium salt in the synthesis of thioethers and guanidinium salts

A novel atom-economic three-component one-pot reaction of a primary amine, an S-alkylisothiouronium salt and a Michael receptor is reported, which affords a guanidinium salt and thioether simultaneously. The guanidine moiety is involved in catalyzing the conjugated Michael addition of the mercaptan. The reaction proceeds under ambient conditions using a non-toxic EtOH-H2O mixture as the solvent, and the two products can be very easily purified. Complete atom economy is achieved by fully utilizing the S-alkylisothiouronium salt and converting the previously wasted mercaptan by-product into the valuable thioether.

E-factor minimized protocols for the polystyryl-BEMP catalyzed conjugate additions of various nucleophiles to α,β-unsaturated carbonyl compounds

Efficient protocols for the addition of carbon-, sulphur- and nitrogen-nucleophiles to α,β-unsaturated carbonyl compounds catalyzed by PS-BEMP have been reported. The adoption of solvent-free conditions (SolFC) was crucial for improving the efficiency of all the processes, while by using an organic reaction medium poor results were obtained. Addition reactions were performed by using equimolar amounts of reagents, and the products were isolated by simple filtration with the minimal amount of organic solvent. This approach allowed the E-factor, a measure of the waste of a reaction, to be minimized. Further waste minimization (95.7% compared to batch protocol) has been accomplished by defining a larger scale continuous-flow protocol operating under SolFC.

Crown ether complex cation ionic liquids: Preparation and applications in organic reactions

A series of crown ether complex cation ionic liquids (CECILs) were designed, synthesised and characterised by NMR spectroscopy, HRMS, thermogravimetric differential thermal analysis (TG-DTA) and elemental analysis. Their applications in various organic reactions were investigated: [15-C-5Na][OH], [15-C-5Na][OAc], [18-C-6K][OH] and [18-C-6K][OAc] (15-C-5=[15]crown-5; 18-C-6=[18]crown-6) efficiently catalysed the Michael addition of alkenes and relevant nucleophiles; [18-C-6K][OH] and [15-C-5Na][OH] effectively catalysed the Henry reaction of nitromethane and aromatic aldehydes; [18-C-6K][OH] has excellent catalytic efficiency for Knoevenagel condensation of aromatic aldehydes and malononitrile; PdCl2/[18-C-6K] 3[PO4]/K2CO3 efficaciously catalysed the Heck reaction of olefins and aromatic halides; [18-C-6K][BrO3] can be used as both oxidant and solvent in the oxidation reaction of aromatic alcohols. The CECIL catalysts [15-C-5Na][OH] (Michael addition) and [18-C-6K][OH] (Henry reaction) can be recycled and reused several times without obvious loss of activity and their recovery is very simple.

Thia-Michael addition using cheap and odorless S-alkylisothiouronium salts as thiol equivalents in water

S-Alkylisothiouronium salt has been found to be a non-toxic, odorless and simply operational alternative of thiol for the thia-Michael addition with electron-deficient olefins. The reactions were carried out under alkaline conditions in water at room temperature within 5-20 minutes to afford the expected products in good to excellent yields. Georg Thieme Verlag Stuttgart.

[HP(HNCH2CH2)3N]NO3: An efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions

In the presence of a catalytic amount of an azaphosphatrane nitrate salt, amines and thiols react readily with Michael acceptors. The salt is also an efficient promoter for the one pot synthesis of α-amino and α-amidonitriles. By anchoring the salt to Merrifield Resin, a reusable heterogeneous catalyst is obtained for these reactions. Evidence is presented for catalysis being attributable solely to the NO3- ion.

KF/Al2O3-mediated Michael addition of thiols to electron-deficient olefins

Potassium fluoride supported on alumina efficiently catalyzes Michael addition of aromatic and aliphatic thiols to a variety of conjugated alkenes such as α,β-unsaturated carbonyl compounds, carboxylic esters, amides, nitriles and chalcones. The Michael adducts are produced in good to excellent yields and relatively in short times. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency. Copyright Taylor & Francis, Inc.

Catalysis by ionic liquid: A simple, green and efficient procedure for the Michael addition of thiols and thiophosphate to conjugated alkenes in ionic liquid, [pmIm]Br

A room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes Michael addition of thiols and diethyl dithiophosphate to a variety of conjugated alkenes such as α,β- unsaturated carbonyl compounds, carboxylic esters,

Catalysis by an ionic liquid: Efficient conjugate addition of thiols to electron deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent-free conditions

An inexpensive and readily available ionic liquid, tetrabutylammonium bromide in the molten state, efficiently catalyzes the conjugate addition of thiols to α,β-unsaturated nitriles, carboxylic ester, ketones and aldehydes as well as nitro olefins.