5816-35-3Relevant academic research and scientific papers
Zn(ii)@TFP-DAQ COF: An efficient mesoporous catalyst for the synthesis of: N -methylated amine and carbamate through chemical fixation of CO2
Sarkar, Priyanka,Chowdhury, Arpita Hazra,Riyajuddin, Sk.,Biswas, Surajit,Ghosh, Kaushik,Islam, Sk. Manirul
, p. 744 - 752 (2020/01/31)
Selective N-methylation and carbamate formation reactions were demonstrated via the chemical incorporation of CO2 using a Zn-loaded TFP-DAQ COF (covalent organic framework) as an active catalyst under mild reaction conditions. The selective N-methylation and N-formylation reactions were performed by simply varying the type of solvent. The Zn(ii)@TFP-DAQ COF catalyst was characterized via different characterization techniques such as PXRD, FTIR, UV-vis, N2 adsorption-desorption studies, FESEM and TEM. The catalyst material showed pores in the mesoporous region with a high surface area of 1117.375 m2 g-1. The as-synthesized material was applied as a cheap catalyst for the N-methylation of secondary amines and in carbamate formation reactions with high yields of the desired products up to 98.5% and 97%, respectively, with >99% selectivity. The catalyst was found to be completely heterogeneous and reusable for multiple reaction cycles.
Modified Graphene Oxide Based Zinc Composite: an Efficient Catalyst for N-formylation and Carbamate Formation Reactions Through CO2 Fixation
Khatun, Resmin,Biswas, Surajit,Islam, Sarikul,Biswas, Imdadul Haque,Riyajuddin, Sk,Ghosh, Kaushik,Islam, Sk Manirul
supporting information, p. 1303 - 1312 (2019/01/25)
Catalytic fixation of CO2 through chemical reactions is always a challenging task of synthetic chemistry. This paper represents the design and synthesis of an eco-friendly low cost zinc metal containing heterogeneous catalyst of aminically modified Graphene Oxide. Characterization of the catalyst has been carried out by Raman and FTIR spectra, AAS, XRD, TEM, SEM, EDX and N2 adsorption desorption studies. It was found that the catalyst was very proficient for the CO2 fixation through N-formylation and carbamate formation reactions of amines. Catalytic N-formylation reaction of both aromatic and aliphatic amines gave high yield of corresponding formylated products in presence of polymethylhydrosiloxane (PMHS) as reducing agent under 1 bar CO2 pressure and mild temperature. Formation of carbamates from aniline or its derivatives and alkyl/aryl bromide with good product selectivity was also achieved under same CO2 pressure in presence of our synthesized catalyst at room temperature with solvent-free condition. The catalyst is reusable and e?cient even after six cycles.
Catalytic synthesis of benzimidazoles and organic carbamates using a polymer supported zinc catalyst through CO2 fixation
Biswas, Imdadul Haque,Biswas, Surajit,Islam, Md Sarikul,Riyajuddin, Sk,Sarkar, Priyanka,Ghosh, Kaushik,Islam, Sk Manirul
, p. 14643 - 14652 (2019/09/30)
Utilization of carbon dioxide in chemical fixation for synthesis of fine chemicals like benzimidazoles, organic carbamates, etc. is in high demand in recent years as carbon dioxide is a cost effective, sustainable, and green renewable C1 source. In this article we present the design and synthesis of an organically modified polystyrene bound heterogeneous [PS-Zn(ii)-SALTETA] catalyst. The catalyst has been characterized thoroughly by Fourier transform infrared spectroscopy, atomic absorption spectroscopy, thermo gravimetric analysis, PXRD, SEM and EDAX studies. The catalyst was used for cyclization of o-phenylenediamines through insertion of carbon dioxide in order to produce benzimidazoles in the presence of dimethylamine borane (DMAB). The developed catalytic procedure is sustainable, economical and efficient owing to the utilization of ethanol/water as a biodegradable and environment friendly solvent system. Besides benzimidazole production the catalyst was also very active for manufacture of organic carbamates from anilines and n-butyl bromide under atmospheric CO2 pressure under solvent free conditions at room temperature and the catalytic protocol showed outstanding functional group tolerance. Moreover the catalyst is highly recyclable and reusable.
One-pot preparation of carbamoyl benzotriazoles and their applications in the preparation of ureas, hydrazinecarboxamides and carbamic esters
Mao, Hui,Liu, Huili,Tu, Yawei,Zhong, Zhiyun,Lv, Xin,Wang, Xiaoxia
, p. 13 - 22 (2016/02/18)
Carbamoyl benzotriazoles were conveniently synthesized in one-pot from carboxylic acids, diphenyl phosphorazidate (DPPA) and 1H-benzotriazole (BtH). The reactivity and applications of carbamoyl benzotriazoles were also explored. Carbamoyl benzotriazoles react smoothly with amino acids, hydrazines and alcohols, thus providing facile access to the corresponding ureas, hydrazinecarboxamides and carbamic esters, respectively, in good to excellent yields.
Metal free oxidative coupling of aryl formamides with alcohols for the synthesis of carbamates
Reddy, N. Veera,Prasad, K. Rajendra,Reddy, P. Sudhir,Lakshmi Kantam,Reddy, K. Rajender
supporting information, p. 2172 - 2175 (2014/04/03)
A direct transformation of N-aryl formamides to the corresponding carbamates via the formation of isocyanate intermediates is achieved in good yields using hypervalent iodine as an oxidant. This journal is
Reaction of organozinc halides with aryl isocyanates
Yang, Haoran,Huang, Danfeng,Wang, Ke-Hu,Xu, Changming,Niu, Teng,Hu, Yulai
supporting information, p. 2588 - 2593 (2013/03/28)
Reformatsky reagent, benzylzinc bromide or alkylzinc iodides react with aryl isocyanates directly to give corresponding N-substituted carbamates under mild reaction conditions. However, the reaction of allylzinc bromide or propargylzinc bromide with aryl isocyanates produces the corresponding N-substituted amides. The reactions provide alternative methods for the synthesis of N-substituted carbamates or amides.
Synthesis of aryl carbamates via copper-catalyzed coupling of aryl halides with potassium cyanate
Yang, Xinye,Zhang, Yihua,Ma, Dawei
supporting information, p. 2443 - 2446,4 (2020/08/31)
Coupling of aryl halides with potassium cyanate takes place at 100-110 °C in alcohols under the catalysis of CuI (cuprous iodide) and 2-(2,6-dimethylphenylamino)-2-oxoacetic acid, affording the corresponding aryl carbamates with great diversity. Copyright
Reactions of Aryl Isocyanates with Alcohols
Bacaloglu, R.,Cotarca, L.,Marcu, N.,Toelgyi, St.
, p. 428 - 434 (2007/10/02)
The reaction of aryl isocyanates with alcohols has been kinetically studied as a model reaction for polyurethane formation under conditions similar to those of industrial scale production.Considering the isocyanate and alcohol structure, kinetic isotopic effect, activation enthalpy and entropy and solvent effects it has been found that the most probable mechanism is the alcohol addition through a four-membered cyclic transition state.
Kinetics and Mechanism of Isocyanate Reactions. II. Reactions of Aryl Isocyanates with Alcohols in the Presence of Tertiary Amines
Bacaloglu, R.,Cotarca, L.,Marcu, N.,Toelgyi, St.
, p. 530 - 540 (2007/10/02)
The reaction of phenyl isocyanate with n-butanol in the presence of tertiary amines has been kinetically studied as a model process for the polyurethane formation under conditions similar to those of industrial scale production.The rate-determining step is belived to be the nucleophilic attack of tertiary amine on an associate of isocyanate with alcohol which is then converted into a very reactive uronium salt.This salt reacts fast with alcohol giving the final product, the urethane.
Kinetics and Mechanism of Isocyanate Reactions. III. Reactions of Aryl Isocyanates with Alcohols in the Presence of Organotin Compounds
Bacaloglu, R.,Cotarca, L.,Marcu, N.,Toelgyi, St.
, p. 541 - 548 (2007/10/02)
A comparative kinetic study for the reaction of aryl isocyanates with alcohols in the presence of organotin compounds has been performed.It has been found that the transfer of an alkoxide ion from tin to isocyanate is the rate-determining step.This transfer occurs within a complex formed in two rapid preequilibrium processes between either tin compounds and alcohol or isocyanate, respectively.
