29518-72-7

Upstream product

• 111-66-0 oct-1-ene 
• 71-43-2 benzene 
• 1188-92-7 Trihexylboran; Tri-n-hexylbor 
• 536-74-3 phenylacetylene 
• 100-42-5 styrene 
• 111-25-1 1-bromo-hexane 
• 111-71-7 heptanal 
• 1083-98-3 diisopropyl benzylphosphonate 
• 938-81-8 N-nitrosoacetanilide 
• 57365-48-7 (Z)-oct-1-enyl(trimethyl)silane 
• 70109-89-6 1-trimethylsiloxyoct-1-ene 
• 50543-74-3 C₂₆H₄₄B^(1-)*Li⁽¹⁺⁾ 
• 157670-36-5 Carbonic acid ethyl ester 1-((E)-styryl)-hexyl ester 
• 7695-69-4 bis(phenylthio)methylbenzene 

Downstream Products

• 78605-96-6 jasminaldehyde 
• 111480-77-4 Phenyl-1,2-octanedione 

Relevant academic research and scientific papers

16-Electron Nickel(0)-Olefin Complexes in Low-Temperature C(sp2)-C(sp3) Kumada Cross-Couplings

Investigations into the mechanism of the low-temperature C(sp2)-C(sp3) Kumada cross-coupling catalyzed by highly reduced nickel-olefin-lithium complexes revealed that 16-electron tris(olefin)nickel(0) complexes are competent catalysts for this transformation. A survey of various nickel(0)-olefin complexes identified Ni(nor)3as an active catalyst, with performance comparable to that of the previously described Ni-olefin-lithium precatalyst. We demonstrate that Ni(nor)3, however, is unable to undergo oxidative addition to the corresponding C(sp2)-Br bond at low temperatures (a nickel(0)-alkylmagnesium complex. We demonstrate that this unique heterobimetallic complex is now primed for reactivity, thus cleaving the C(sp2)-Br bond and ultimately delivering the C(sp2)-C(sp3) bond in high yields.

Recyclable and reusable PdCl2(PPh3)2/PEG-400/H2O system for the hydrophenylation of alkynes with sodium tetraphenylborate

A stable and efficient PdCl2(PPh3)2/PEG-400/H2O catalytic system for the hydrophenylation reaction of alkynes has been developed. In the presence of 3 mol% PdCl2(PPh3)2 and 2 equiv. of HOAc, the hydrophenylation of both terminal and internal alkynes with sodium tetraphenylborate proceeded smoothly in a mixture of PEG-400 and water at room temperature or 50 °C to afford a variety of phenyl-substituted alkenes in moderate to high yields. The isolation of the products was easily performed by extraction with petroleum ether, and the PdCl2(PPh3)2/PEG-400/H2O system could be readily recycled and reused six times without apparent loss of catalytic activity.

Enantio- and Regioselective NiH-Catalyzed Reductive Hydroarylation of Vinylarenes with Aryl Iodides

A highly enantio- and regioselective hydroarylation process of vinylarenes with aryl halides has been developed using a NiH catalyst and a new chiral bis imidazoline ligand. A broad range of structurally diverse, enantioenriched 1,1-diarylalkanes, a structure found in a number of biologically active molecules, have been obtained with excellent yields and enantioselectivities under extremely mild conditions.

Iron-catalyzed cross-coupling reaction: Heterogeneous palladium and copper-free Heck and Sonogashira cross-coupling reactions catalyzed by a reusable Fe(III) complex

An interesting silica-supported iron catalyst was successfully prepared and demonstrated as an efficient heterogeneous catalyst for cross-coupling reactions of aryl halides. The as-prepared nanocatalyst was well characterized and found to be highly efficient in Heck reaction under mild and sustainable conditions (water as solvent at 80?°C in short reaction time). Furthermore, the obtained catalyst was used as an efficient, inexpensive and green heterogeneous catalyst for Sonogashira cross-coupling reactions of various aryl iodides and provided the corresponding products with moderate to good yields. This phosphine, copper and palladium-free catalyst was simply recovered from the reaction mixture and recycled five times without substantial decrease in its catalytic activity.

Oxygenation of Simple Olefins through Selective Allylic C?C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes

A novel metal-free allylic C?C σ-bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2-Aryl or alkyl migration through allylic C?C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O-atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal-free conditions, and high regio- and stereoselectivity.

Immobilized NNN Pd-complex on magnetic nanoparticles: Efficient and reusable catalyst for Heck and Sonogashira coupling reactions

A highly efficient and easily recyclable magnetic nanoparticle supported palladium catalyst was developed and applied in the Heck and Sonogashira reactions in order to show its catalytic applicability in Pd-catalyzed C-C coupling protocols. The catalyst was prepared using a simple chemical process. First, the prepared Fe3O4@SiO2 nanoparticles were reacted with (3-chloropropyl)-trimethoxysilane (3-CPTMS) in order to synthesis chloro-functionalized magnetic nanoparticles (CPS-MNPs). The substitution reaction of synthetic NNN ligand with CPS-MNPs yields the production of CPS-MNPs-NNN ligand. Finally, immobilization of palladium species on CPS-MNPs-NNN ligand surface afforded CPS-MNPs-NNN-Pd catalyst. The structure and morphology of the prepared nanocatalyst was characterized using various methods such as SEM, TEM, XPS, EDX, CHN, ICP, XRD, FT-IR and VSM techniques. The TEM images show that the sizes of the palladium catalyst are in the range of 8-15 nm. The Heck and Sonogashira coupling reactions were performed in the presence of a catalytic amount of this catalyst system (0.5 mol%) and good yields of products were obtained. Due to the magnetic nature of the catalyst it can be separated from the reaction mixture easily by applying an external magnetic field. Heterogeneity tests affirmed that the catalytic activity stayed indefectible during multiple reaction cycles.

Single-site palladium(II) catalyst for oxidative heck reaction: Catalytic performance and kinetic investigations

The development of organometallic single-site catalysts (SSCs) has inspired the designs of new heterogeneous catalysts with high efficiency. Nevertheless, the application of SSCs in certain modern organic reactions, such as C-C bond formation reactions, has still been less investigated. In this study, a single-site Pd(II) catalyst was developed, where 2,2′-bipyridine-grafted periodic mesoporous organosilica (PMO) was employed as the support of a Pd(II) complex. The overall performance of the single-site Pd(II) catalyst in the oxidative Heck reaction was then investigated. The investigation results show that the catalyst displays over 99% selectivity for the product formation with high reaction yield. Kinetic profiles further confirm its high catalytic efficiency, showing that the rate constant is nearly 40 times higher than that for the free Pd(II) salt. X-ray absorption spectroscopy reveals that the catalyst has remarkable lifetime and recyclability.

Synthesis of new surfactant-like triazine-functionalized ligands for Pd-catalyzed Heck and Sonogashira reactions in water

In this study, a novel class of ligands for palladium-catalyzed C-C coupling reactions in water is introduced. A range of triazine-functionalized ligands were synthesized using 2,4,6-trichloro-1,3,5-triazine (TCT) reagent. Among them, N2,N4,N6-tridodecyl-1,3,5-triazine-2,4,6-triamine (TDTAT) was found to be an efficient ligand for the Pd-catalyzed Heck and Sonogashira reactions in water, which acted as a green solvent. TEM analysis showed that in the presence of TDTAT in water at 80°C, PdCl2 is converted to nanoparticles with an average size of ～3 nm. The formed Pd-nanoparticles act as efficient catalytic species for C-C bond formation reactions in neat water. Under these conditions, Pd-catalyzed Heck and Sonogashira reactions are accomplished without the need for phosphine ligand. The generation of emulsion droplets (5-10 μm) containing Pd(0) nanoparticles would function as an effective reactor to accelerate the rate of the reaction in water media.

A one-pot tandem olefin isomerization/metathesis-coupling (ISOMET) reaction

A tandem catalytic reaction has been developed as part of a process to discover tungsten-based olefin metathesis catalysts that have a strong preference for terminal olefins over cis or trans internal isomers in olefin metathesis. This tandem isomerization/terminal olefin metathesis reaction (ISOMET) converts Cn trans internal olefins into C2n-2cis olefins and ethylene. This reaction is made possible with Ru-based "alkene zipper" catalysts, which selectively isomerize trans olefins to an equilibrium mixture of trans and terminal olefins, plus tungsten-based metathesis catalysts that react relatively selectively with terminal olefins to give Z homocoupled products. The most effective catalysts are W(NAr)(C3H6)(pyr)-(OHIPT) (Ar = 2,6-diisopropylphenyl; pyr = pyrrolide; OHIPT = O-2,6-(2,4,6-i-Pr3C6H2)2C6H3) and various [CpRu(P - N)(MeCN)]X (X-= [B(3,5-(CF3)2C6H3)4]-, PF6-, B(C6F5)4-) isomerization catalysts.

Nickel-catalyzed Mizoroki-Heck reaction of aryl sulfonates and chlorides with electronically unbiased terminal olefins: High selectivity for branched products

Achieving high selectivity in the Heck reaction of electronically unbiased alkenes has been a longstanding challenge. Using a nickel-catalyzed cationic Heck reaction, we were able to achieve excellent selectivity for branched products (≥19:1 in all cases) over a wide range of aryl electrophiles and aliphatic olefins. A bidentate ligand with a suitable bite angle and steric profile was key to obtaining high branched/linear selectivity, whereas the appropriate base suppressed alkene isomerization of the product. Although aryl triflates are traditionally used to access the cationic Heck pathway, we have shown that, by using triethylsilyl trifluoromethanesulfonate, we can effect a counterion exchange of the catalytic nickel complex, such that cheaper and more stable aryl chlorides, mesylates, tosylates, and sulfamates can be used to yield the same branched products with high selectivity. Branching out: A Ni-catalyzed Heck reaction for the preparation of 1,1-disubstituted alkenes is presented. High selectivity for the branched products is achieved with electronically unbiased aliphatic terminal olefins. Regioselectivities remain consistently high (≥19:1) throughout. TESOTf=triethylsilyl trifluoromethanesulfonate. Copyright