19310-31-7Relevant academic research and scientific papers
Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide
Ojha, Subhadra,Panda, Niranjan
supporting information, p. 1292 - 1298 (2022/02/19)
A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is
A Straightforward, Purification-Free Procedure for the Synthesis of Ando and Still-Gennari Type Phosphonates
Janicki, Ignacy,Kie?basiński, Piotr
, p. 378 - 382 (2021/10/21)
Z-Selective Still-Gennari and Ando modifications of the typically E-selective Horner-Wadsworth-Emmons reaction are highly valuable synthetic tools in organic chemistry. These procedures are based on application of bis(2,2,2-trifluoroethyl) phosphonates or diaryl phosphonates, respectively, for the olefination of carbonyl groups. In our research, we present an improved, straightforward, purificationfree procedure for the synthesis of these reagents. The key step of our procedure is the reaction of phosphonic dichlorides with the appropriate sodium alkoxides, which results in 52-97% isolated yields of the desired products on a gram scale. The whole three-step process is performed in one pot. Most importantly, the product is obtained in over 95% purity after simple extraction, avoiding column chromatography and distillation. Moreover, we present the synthesis of a novel Still-Gennari type reagent, bis(1,1,1,3,3,3-hexafluoroisopropyl) phosphonates, which may exhibit improved Z-selectivity in Still-Gennari olefinations.
Triazine-hyperbranched polymer-modified magnetic nanoparticles-supported nano-cobalt for C–C cross-coupling reactions
Hajipour, Abdol R.,Sadeghi, Shaghayegh
, p. 3219 - 3233 (2021/08/06)
Design of hyperbranched polymers (HBPs) and crafting them in catalytic systems especially in organic chemistry are a relatively unexplored domain. This paper reports the utilization of triazine-hyperbranched polymer (THBP)-coated magnetic chitosan nanoparticles (MCs) as stabilizing matrix for cobalt nanoparticles. Cobalt nanoparticles were fabricated by coordination cobalt(II) ions with amine-terminated triazine polymer and then reduced into Co(0) using sodium borohydride in aqueous medium. The Co(0)-THBP@MCs were fully characterized by FT-IR, SEM–EDX, TEM, and TGA analyses. The presence of metallic cobalt was determined by ICP and XRD techniques. This novel hyperbranched polyaromatic polymer-encapsulated cobalt nanoparticles showed high catalytic activity in Mizoroki–Heck and Suzuki–Miyaura cross-coupling reactions. Heck and Suzuki reactions were carried out using 0.35 and 0.4?mol% of cobalt nanoparticles in which the turnover number (TON) values were calculated as 271 and 225, respectively. In addition, the produced heterogeneous catalyst could be recovered and reused without considerable loss of activity. Oxygen stability and high reusability over 7 runs with trace leaching of the cobalt into the reaction media as well as moisture stability of the immobilized cobalt nanoparticles are their considerable worthwhile advantages.
Pd salen complex@CPGO as a convenient, effective heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions
Ghabdian, Mahdieh,Nasseri, Mohammad Ali,Allahresani, Ali,Motavallizadehkakhky, Alireza
, p. 1713 - 1728 (2018/05/25)
A Pd(II) Schiff base complex supported on graphene oxide nanosheets (Pd(II) salen@CPGO) has been synthesized and characterized by FT-IR, ICP-AES, XRD, SEM/EDX and TEM. The synthesized nanocatalyst has been found to be an efficient heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki coupling reactions. Pd(II) salen@CPGO could be separated and recovered easily from the reaction mixture and recycled several times without a discernible decrease in its catalytic activity. The construction of a solid sheet-supported Pd catalyst would be expected to be a promising system to perform heterogeneous catalytic reactions.
Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water
Drikermann, Denis,Kupfer, Stephan,Seifert, Fabian,Steinmetzer, Johannes,Vilotijevic, Ivan,Zi, You
, p. 6092 - 6097 (2021/07/21)
Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.
Promising new catalytic properties of a Co (II)-carboxamide complex and its derived Co3O4 nanoparticles for the Mizoroki-Heck and the Epoxidation reactions
Kiani, Mahsa,Bagherzadeh, Mojtaba,Meghdadi, Soraia,Fadaei-Tirani, Farzaneh,Babaie, Maryam,Schenk-Jo?, Kurt
, (2020/07/13)
The new Co(II) - carboxamide complex (1) and Co3O4 nanoparticles (2), by way of thermal decomposition of (1) have been efficiently synthesised in the environment-friendly. X-ray diffraction reveals a slightly distorted octahedral coordination of cobalt (four nitrogens and two oxygens) in (1) and regular octahedral or tetrahedral ones (oxygens only) in (2). The investigation of (1) and (2) in the Mizoroki-Heck and epoxidation of alkens reactions showed them both to be powerful, green and inexpensive catalysts.
Novel and efficient polymer supported copper catalyst for heck reaction
Anas, Saithalavi,Anjali, Suresh,Sruthi, Pambingal Rajan,Varghese, Nicy
, (2020/07/08)
A novel polymer supported copper complex (m-PAN-Cu) is prepared by immobilizing Cuprous Iodide (CuI) on amidoxime modified Polyacrylonitrile (mPAN) and characterised by FTIR, XRD, EDX, ICP-MS and XPS analyses. This complex was further explored as a general and efficient heterogeneous catalyst for Heck coupling reaction of a series of aryl halides with olefins and afforded the corresponding coupling products in moderate to good yields. This catalyst offers easy preparation, good stability, excellent catalytic activity and reusability. This is the first study involving an amidoxime modified PAN supported copper catalyst towards greener and efficient Heck reaction.
Synthesis and characterization of mesoporous organosilica supported palladium (SBA-Pr-NCQ-Pd) as an efficient nanocatalyst in the Mizoroki–Heck coupling reaction
Moradi, Razieh,Mohammadi Ziarani, Ghodsi,Badiei, Alireza,Mohajer, Fatemeh
, (2020/10/02)
In the present study, the modification of a mesoporous organosilica nanocomposite SBA-15 (Santa Barbara Amorphous 15) was carried out in two steps, first through the surface functionalization of SBA-Pr-NH2 with 2-chloroquinoline-3-carbaldehyde to form SBA-Pr-NCQ, and then through a post-modification process with palladium ions. The target nanocompound structure of SBA-Pr-NCQ-Pd was characterized by different techniques (thermogravimetric analysis, X-ray diffraction, scanning electron microscopy, Energy-dispersive X-ray spectroscopy (EDX), and Fourier transform infrared spectroscopy). The catalytic performance of the porous inorganic–organic hybrid nanocomposite (SBA-Pr-NCQ-Pd) in one of the most important carbon–carbon bond-forming processes, the Mizoroki–Heck coupling reaction of aryl halides and methacrylate in water/ethanol media, was examined. Compared to previous reports, this protocol afforded some advantages, such as high yields of products, short reaction times, catalyst stability without leaching, simple methodology, easy workup, and greener conditions. Also, the nanocatalyst can be easily separated from the reaction mixture and reused several times without a significant decrease in activity and promises economic as well as environmental benefits.
Synthesis and characterization of a new bis-NHC palladium complex and its catalytic activity in the Mizoroki–Heck reaction
Cui, Jin,Feng, Can,Liu, Cheng-Xin,Wang, Yu-Fang,Zhang, Ming-Jie
, p. 684 - 688 (2020/05/22)
A new bis-N-heterocyclic carbene palladium complex, (C13H9N2F2)2PdCl2, is synthesized by a three-step reaction and characterized by 1H NMR and 13C NMR spectroscopy as well as by X-ray crystallography. This new bis-N-heterocyclic carbene palladium complex has excellent stability and is capable of efficiently catalyzing the Mizoroki–Heck coupling reaction of aryl halides with acrylates.
Biogenic synthesis of palladium nanoparticles using Boswellia sarrata and their applications in cross-coupling reactions
Arde, Satyanarayan M.,Rashinkar, Gajanan S.,Jadhav, Sanjay N.,Patil, Audumbar D.,Salunkhe, Rajashri S.
, (2020/10/02)
A facile and green route for biogenic synthesis of palladium nanoparticles (PdNPs) using aqueous extract of nontoxic and renewable Boswellia sarrata leaves is reported. The as-synthesized PdNPs were systematically characterized by using ultraviolet (UV)–visible spectroscopy, X-ray diffraction analysis, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, and X-ray photoelectron spectroscopy. The PdNPs were crystalline and cubic in nature with average particle size of ~6 nm and successfully employed as heterogeneous catalyst in the Suzuki–Miyaura and Mizoroki–Heck cross-coupling reactions. The PdNPs could be recycled up to five times with modest change in the catalytic activity.
