1608-36-2

Usage

Synthesis Reference(s)

Synthetic Communications, 24, p. 2069, 1994 DOI: 10.1080/00397919408010217Tetrahedron Letters, 28, p. 801, 1987 DOI: 10.1016/S0040-4039(01)80993-X

InChI:InChI=1/C10H9NO4/c1-15-10(12)7-4-8-2-5-9(6-3-8)11(13)14/h2-7H,1H3/b7-4+

Upstream product

• 67-56-1 methanol 
• 619-89-6 p-nitrocinnamic acid 
• 621-82-9 Cinnamic acid 
• 103-26-4 methyl cinnamate 
• 555-16-8 4-nitrobenzaldehdye 
• 96-32-2 bromoacetic acid methyl ester 
• 70372-55-3 1,1-dibromo-2-(4-nitrophenyl)cyclopropane 
• 67-63-0 isopropyl alcohol 
• 61921-33-3 p-nitrocinnamoyl chloride 
• 103-26-4 Methyl cinnamate 
• 292638-85-8 acrylic acid methyl ester 
• 586-78-7 para-nitrophenyl bromide 
• 15450-93-8 3-methyl-1-phenyl-3-phospholene 
• 7564-51-4 2,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide 

Downstream Products

• 35418-07-6 methyl 3-(4-aminophenyl)propionate 
• 82297-28-7 dimethyl 4,4'-azoxycinnamate 
• 78727-98-7 α-nitro-β-(4-nitrophenyl)acrylic acid methyl ester 
• 52883-45-1 3,3-dimethyl-5-(4-nitro-phenyl)-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one 
• 81928-74-7 (E) methyl α-nitro paranitrocinnamate 
• 65198-02-9 3-(4-aminophenyl)-acrylic acid methyl ester 
• 113436-52-5 (3S,4R,5R)-4-Nitro-3-(4-nitro-phenyl)-1,5-diphenyl-pyrrolidine-2,2,4-tricarboxylic acid trimethyl ester 
• 1084889-77-9 4-(4-nitrophenyl)-3,4-dihydro-1H-quinolin-2-one 
• 851321-54-5 2-methoxy-4-p-nitrophenyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitrile 
• 1298083-10-9 ethyl 5-(4-nitrophenyl)-2-phenylpentanoate 
• 1298083-14-3 ethyl 5-(4-aminophenyl)-2-phenylpentanoate 
• 1298083-18-7 ethyl 5-(4-azidophenyl)-2-phenylpentanoate 
• 1298083-23-4 ethyl 4-(4-aminophenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxylate 
• 20716-25-0 3-(4-nitrophenyl)-1-propanol 

Relevant academic research and scientific papers

Organically modified Pd-silica catalysts applied in Heck coupling

Pd-silica catalysts prepared by depositing Pd onto silica precursors modified by surface methyl or phenyl groups through the reduction of Pd 2+ ions with surface Si-H functions exhibit high activity and selectivity in Heck coupling.

Thiophene based imino-pyridyl palladium(II) complexes: Synthesis, molecular structures and Heck coupling reactions

The new compounds (5-methyl-2-thiophene-2-pyridyl(R))imine [R = methyl (L1); R = ethyl (L2)] and (5-bromo-2-thiophene-2-pyridyl(R)imine [R = methyl (L3); R = ethyl (L4)] were successfully synthesized via Schiff base condensation reaction and obtained in g

Palladium-Loaded Cucurbit[7]uril-Modified Iron Oxide Nanoparticles for C?C Cross-Coupling Reactions

Cucurbit[7]uril modified iron oxide nanoparticles (CB[7]NPs) were loaded with palladium to form nano-catalysts (Pd@CB[7]NPs) that, with microwave heating, catalysed Suzuki–Miyaura, Sonogashira, and Mizoroki–Heck cross-coupling reactions. Reactions were run in environmentally benign 1:1 ethanol/water solvent under convenient aerobic conditions. In a preliminary screening, conversions and yields were uniformly high with turn over frequencies (TOF) ranging from 64 to 7360 h?1. The nano-catalysts could be recovered with a magnet and reused several times (6 times for Suzuki–Miayura reaction) without loss of activity.

Synthesis and structure of palladium 1,2,3-triazol-5-ylidene mesoionic carbene PEPPSI complexes and their catalytic applications in the mizoroki-heck reaction

New mono- and bimetallic 1,2,3-triazol-5-ylidene mesoionic carbene (MIC) complexes of Pd have been synthesized, isolated, and characterized. We have described the synthesis of a bis(MIC) complex via transmetalation from a Ag-MIC complex and two PEPPSI-type complexes which are directly available from their respective triazolium salts by treatment with PdCl2 in pyridine. The X-ray structures are reported for all complexes described herein. Interestingly, each complex described exhibits various secondary noncovalent interactions in the solid state of the general type C-H...Cl, which appear to be important for the stabilization of the solid-state structure of the complexes. We further demonstrated the utility of the new PEPPSI complexes in the Mizoroki-Heck reaction. In the case of aryl iodides and electron-deficient bromides, high conversion is observed with methyl acrylate. Hg poisoning tests suggest that, even with an easily dissociated ligand, the reaction likely proceeds via Pd nanoparticles.

Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide

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

Triazine-hyperbranched polymer-modified magnetic nanoparticles-supported nano-cobalt for C–C cross-coupling reactions

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

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.

Visible-light-induced selective aerobic oxidation of sp3 C-H bonds catalyzed by a heterogeneous AgI/BiVO4 catalyst

An efficient oxidation of sp3 C-H bonds to esters and ketones has been developed using AgI/BiVO4 as the photocatalyst and O2 as the oxidant in water. Various substrates can be transformed into the desired esters and ketones in moderate to good yields. The synthetic utility of this approach has been demonstrated by gram-level experiments and consecutive oxidation experiments. A plausible mechanism has been proposed.

Promising new catalytic properties of a Co (II)-carboxamide complex and its derived Co3O4 nanoparticles for the Mizoroki-Heck and the Epoxidation reactions

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

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.