17425-14-8

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 71-36-3 butan-1-ol 
• 15093-54-6 N-phenyl-1-morpholinethiocarbamide 
• 2762-59-6 N-phenylpiperidine-1-carbothioamide 
• 7442-11-7 N,N-diethyl-N'-phenylthiourea 
• 591-50-4 iodobenzene 
• 692-99-9 O-1-butyl thiocarbamate 
• 108-86-1 bromobenzene 
• 108-90-7 chlorobenzene 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

An Fe3O4@SiO2/Schiff base/Cu(ii) complex as an efficient recyclable magnetic nanocatalyst for selective mono: N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids

An efficient, convenient and novel method for the selective mono N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids in the presence of a recyclable magnetic Cu(ii) nanocatalyst is described. A variety of mono N-arylated O-alkyl thiocarbamates and O-alkyl carbamates were prepared in good to excellent yields with a broad range of aryl coupling partners. The magnetic nanocatalyst can be easily recovered with an external magnetic field and reused at least five times without noticeable leaching or loss of its catalytic activity. This cost-effective and eco-friendly methodology has some other advantages, such as easy preparation of the catalyst, simple workup procedure, and easy purification, which makes this protocol interesting for the users in various fields of pharmacology and biotechnology systems.

Highly Active Dinuclear Titanium(IV) Complexes for the Catalytic Formation of a Carbon-Heteroatom Bond

A series of mononuclear titanium(IV) complexes with the general composition κ3-[R{NHPh2P(X)}2Ti(NMe2)2] [R = C6H4, X = Se (3b); R = trans-C6H10, X = S (4a), Se (4b)] and [{κ2-N(PPh2Se)2}2Ti(NMe2)2] (6b) and two dinuclear titanium(IV) complexes, [C6H4{(NPh2PS)(N)}Ti(NMe2)]2 (3c) and [{κ2-N(PPh2Se)}Ti(NMe2)2]2 (6c), are reported. Dinuclear titanium(IV) complex 6c acts as an efficient catalyst for the chemoselective addition of an E-H bond (E = N, O, S, P, C) to heterocumulenes under mild conditions. The catalytic addition of aliphatic and aromatic amines, alcohol, thiol, phosphine oxide, and acetylene to the carbodiimides afforded the corresponding hydroelemented products in high yield at mild conditions with a broader substrate scope. The catalytic efficiency of the dinuclear complex depends on the cooperative effect of the TiIV ions, the systematic variation of the intermetallic distance, and the ligand's steric properties of the complex, which enhances the reaction rate. Most interestingly, this is the first example of catalytic insertion of various E-H bonds into the carbodiimides using a single-site catalyst because only the titanium-mediated insertion of E-H into a C-N unsaturated bond is reported to date. The amine and alcohol insertion reaction with the carbodiimides showed first-order kinetics with respect to the titanium(IV) catalyst as well as substrates. A most plausible mechanism for hydroelementation reaction is also proposed, based on the spectroscopic data of the controlled reaction, a time-course study, and the Hammett plot.

Computational tools for mechanistic discrimination in the reductive and metathesis coupling reactions mediated by titanium(IV) isopropoxide

A theoretical study has been carried out at the B3LYP/LANL2DZ level to compare the reactivity of phenyl isocyanate and phenyl isothiocyanate towards titanium(IV) alkoxides. Isocyanates are shown to favour both mono insertion and double insertion reactions. Double insertion in a head-to-tail fashion is shown to be more exothermic than double insertion in a head-to-head fashion. The head-to-head double insertion leads to the metathesis product, a carbodiimide, after the extrusion of carbon dioxide. In the case of phenyl isothiocyanate, calculations favour the formation of only mono insertion products. Formation of a double insertion product is highly unfavourable. Further, these studies indicate that the reverse reaction involving the metathesis of N,N ′-diphenyl carbodiimide with carbon dioxide is likely to proceed more efficiently than the metathesis reaction with carbon disulphide. This is in excellent agreement with experimental results as metathesis with carbon disulphide fails to occur. In a second study, multilayer MM/QM calculations are carried out on intermediates generated from reduction of titanium(IV) alkoxides to investigate the effect of alkoxy bridging on the reactivity of multinuclear Ti species. Bimolecular coupling of imines initiated by Ti(III) species leads to a mixture of diastereomers and not diastereoselective coupling of the imine. However if the reaction is carried out by a trimeric biradical species, diastereoselective coupling of the imine is predicted. The presence of alkoxy bridges greatly favours the formation of the d,l (±) isomer, whereas the intermediate without alkoxy bridges favours the more stable meso isomer. As a bridged trimeric species, stabilized by bridging alkoxy groups, correctly explains the diastereoselective reaction, it is the most likely intermediate in the reaction.

A one-pot conversion of di-substituted thiourea to O-organyl arylthiocarbamate using FeCl3

Unsymmetrical thiourea, which on demand can generate isothiocyanate in the presence of FeCl3, can serve as a latent isothiocyanate functionality and circumvent the difficulties associated with the direct use of reactive isothiocyanate functiona

Effect of successive increase in alcohol chains on reaction with isocyanates and isothiocyanates

The reaction of isocyanates and isothiocyanates with long-chain alcohols, e.g. n-hexanol, n-heptanol and n-octanol, exclusively gave N-aryl-O-alkyl carbamates, while N-aryl-O-alkyl carbamates were formed along with symmetrical 1,3-disubstituted ureas and thioureas when the same reactions were carried out with small-chain alcohols at room temperature without using any solvent.

Expeditious routes to 4-alkoxyquinazoline-2-carbonitriles and thiocarbamates via N-arylimino-1,2,3-dithiazoles using microwave irradiation

Conversion of N-arylimino-4-chloro-5H-1,2,3-dithiazole 11 into the 4- alkoxyquinazoline-2-carbonitriles 13a-i and of the aryl isothiocyanates 15 into aryl thiocarbamates 16a-j with sodium alkoxides in the corresponding alcohol, either by conventional ther

An efficient organotin (IV) catalyst towards the syntheses of thiourethanes

Dibenzyltin(IV) diacetate catalyses the reactions of phenyl isothiocyanate and various alcohols in refluxing benzene giving rise to the corresponding thiourethanes in excellent yields.