875312-97-3Relevant academic research and scientific papers
Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides
Hajiloo Shayegan, Mojtaba,Li, Zhong-Yuan,Cui, Xin
, (2021/12/02)
Ligand-controlled regiodivergence has been developed for catalytic semireduction of allenamides with excellent chemo- and stereocontrol. This system also provides an example of catalytic regiodivergent semireduction of allenes for the first time. The divergence of the semireduction is enabled by ligand switch with the same palladium pre-catalyst under operationally simple and mild conditions. Monodentate ligand XPhos exclusively promotes selective 1,2-semireduction to afford allylic amides, while bidentate ligand BINAP completely switched the regioselectivity to 2,3-semireduction, producing (E)-enamide derivatives.
Straightforward synthesis, spectroscopic characterizations and comprehensive DFT calculations of novel 1-ester 4-sulfonamide-1,2,3-triazole scaffolds
Alizadeh, Maryam,Mirjafary, Zohreh,Saeidian, Hamid
, (2019/12/06)
For the first time, an efficient click azide?alkyne [3 + 2] cycloaddition reaction for synthesis of new 1-ester 4-sulfonamide-1,2,3-triazole derivatives was developed via a three-component reaction of N-propargylsulfonamides, sodium azide, and α-haloesters in a one pot method. The mild reaction conditions, avoiding the isolation of hazardous organic azides, good yields (65–78%), and commercially available and inexpensive starting materials are advantages of this cycloaddition reaction for synthesis of fine chemicals. The all desired products were characterized by FT-IR, 1H and 13C NMR spectroscopy. The HOMO-LUMO analysis (electrophilicity index), vibrational frequencies (FT-IR), 1H and 13C chemical shift values and Li+ and Na+ ion affinities of a desired product have been also calculated by density functional theory (DFT). Lithium ion affinity of the product was determined as 80.78 kJ/mol higher than its sodium ion affinity. The NICS index was used to confirm of the cation π interaction in complex of the synthesized product with Li+ and Na+ ions.
Efficient synthesis, spectroscopic characterization and DFT based studies of novel 1-amide 4-sulfonamide-1,2,3-triazole derivatives
Bonyad, Sarvenaz Rouhi,Mirjafary, Zohreh,Saeidian, Hamid,Rouhani, Morteza
, p. 164 - 170 (2019/07/18)
In the present study, for the first time 1-amide 4-sulfonamide-1,2,3-triazole scaffolds were synthesized by using an azide-alkyne Huisgen cycloaddition reaction. The target products were obtained in moderate to good yields (45–75%) by using catalytic CuI and green system H2O/EtOH. The easy availability of the inexpensive starting materials, avoiding isolation and handling of hazardous organic azides and mild reaction conditions make this method a valuable tool for generating functionalized 1,2,3-triazole derivatives. The unambiguous characterization of synthesized compounds was accomplished by using various spectroscopic techniques such as 1H NMR, 13C NMR, and FT-IR. The information regarding optimized geometry, were obtained by applying DFT/B3LYP-6-31G(d) method. The electrophilicity index, 1H and 13C chemical shift values, lithium and sodium ion affinities of the desired product 3b have been also calculated by the mentioned method. As a whole, the calculated results were found in close agreement to that of experimental data. The studies revealed that the compound 3b possesses good Li+ and Na+ affinity and cation π interaction plays a vital role in the complexation of 3b. For the first time, nucleus–independent chemical shift index was used to confirm the cation π interaction of 3b.
Copper-catalysed hydroamination of N-allenylsulfonamides: The key role of ancillary coordinating groups
Blieck, Rémi,Perego, Luca Alessandro,Ciofini, Ilaria,Grimaud, Laurence,Taillefer, Marc,Monnier, Florian
supporting information, p. 1225 - 1234 (2019/02/26)
A copper-catalysed hydroamination reaction of N-allenylsulfonamides with amines has been developed through a rational approach based on mechanistic studies. The reaction is promoted by a simple copper(I) catalyst and proceeds at room temperature with complete regioselectivity and excellent stereoselectivity towards linear (E)-N-(3-aminoprop-1-enyl)sulfonamides. Density Functional Theory (DFT) studies allow interpreting the key role of unsaturated substituents on nitrogen as ancillary coordinating moieties for the copper catalyst.
Gold-Catalyzed 1,2-Oxyalkynylation of N-Allenamides with Ethylnylbenziodoxolones
Banerjee, Somsuvra,Senthilkumar, Beeran,Patil, Nitin T.
supporting information, p. 180 - 184 (2019/01/11)
A gold-catalyzed 1,2-oxyalkynylation of N-allenamides with ethylnylbenziodoxolones (EBXs) has been achieved for the first time. The reaction, which follows a redox-neutral Au(I)/Au(III) catalytic pathway, was enabled in an attempt to exhaust the EBX reagents atom-economically by putting the nucleophilic carboxylate part of EBXs to appropriate use. This constitutes the first example for gold-catalyzed β-alkynylation of N-allenamides to construct highly valuable 1,3-enynes. The potential of the sequence is further documented by some follow-up transformations.
Versatile and green synthesis, spectroscopic characterizations, crystal structure and DFT calculations of 1,2,3?triazole?based sulfonamides
Saeidian, Hamid,Sadighian, Hamed,Abdoli, Morteza,Sahandi, Morteza
, p. 73 - 78 (2016/11/25)
A green, and practically reliable method for the synthesis of novel 1,2,3?triazole-based sulfonamides via copper (I)?catalyzed azide?alkyne [3 + 2] cycloaddition reaction was reported. The desired products were characterized by CHN analysis, FT-IR, 1H and 13C NMR, ESI-MS spectroscopy, single crystal X-ray diffraction and density functional theory (DFT) geometry optimization and molecular orbital calculations. Mild and green reaction conditions, atom-economic and high yields (61–91%) make this protocol an attractive option for the synthesis of 1,2,3?triazoles bearing sulfonamide moiety. Geometrical structures, vibrational frequencies, 1H and 13C chemical shift values, Mulliken charge distribution and electrophilicity index (HOMO-LUMO analysis) of the characterized structure of 3f in the ground state have been calculated with the aid of DFT studies. The calculated chemical shifts (NMR) and vibrational frequencies (FT-IR) are in compliance with the experimental findings. The aim of the DFT study was to make a reasonable assignment of vibrational bands and chemical shifts.
Efficient synthesis of novel 1,3-diyne-based sulfonamides using CuCl2/Et3N as a robust catalytic system
Mirjafary, Zohreh,Sadighian, Hamed,Piri, Samira,Saeidian, Hamid
, p. 188 - 194 (2017/03/07)
An efficient and practical synthesis of 1,3-diyne-based sulfonamides using CuCl2/Et3N as a catalytic system is disclosed. Mild reaction conditions, atom-economy and high yields (50–91%) make this method an attractive option for the preparation of 1,3-diyne-based sulfonamide derivatives.
[3+2]-Annulation of platinum-bound azomethine ylides with distal C=C bonds of N-allenamides
Chakrabarty, Indradweep,Inamdar, Suleman M.,Akram, Manjur O.,Gade, Amol B.,Banerjee, Subhrashis,Bera, Saibal,Patil, Nitin T.
supporting information, p. 196 - 199 (2016/12/27)
A Pt-catalyzed, highly regioselective reaction between N-allenamides and imino-alkynes leading to pyrrolo[1,2-a]indoles is described. This represents the first example of [3+2]-annulation of Pt-bound azomethine ylides with the distal C=C bond of N-allenam
Highly Efficient One-Pot Synthesis of Novel Propargylamine-Based Sulfonamides by an A3-Coupling Reaction
Abdoli, Morteza,Saeidian, Hamid,Kakanejadifard, Ali
, p. 2473 - 2476 (2016/10/24)
Novel propargylamine-based sulfonamides were synthesized in excellent yields by the copper(I) iodide catalyzed three-component coupling of propargylsulfonamides, morpholine, and aldehydes.
Gold-Catalyzed Fluorination–Hydration: Synthesis of α-Fluorobenzofuranones from 2-Alkynylphenol Derivatives
Wang, Qiang,Jiang, Yu,Sun, Run,Tang, Xiang-Ying,Shi, Min
supporting information, p. 14739 - 14745 (2016/10/03)
The AuI-catalyzed fluorination–hydration of 2-alkynylphenol derivatives in the presence of Selectfluor [1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate)] has been developed. This method provides straightforward a
