62924-88-3

Upstream product

• 106-38-7 para-bromotoluene 
• 98-83-9 isopropenylbenzene 
• 98-86-2 acetophenone 
• 1391948-74-5 (4-methylphenyl)ethynyl ethyl sulfide 
• 99-99-0 1-methyl-4-nitrobenzene 
• 624-31-7 4-tolyl iodide 
• 109141-70-0 1-(1-methoxyprop-1-en-2-yl)benzene 
• 380481-66-3 5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane 
• 1427318-09-9 C₁₁H₁₃ClS 
• 1427318-40-8 C₁₇H₁₈S 
• 676-58-4 methylmagnesium chloride 
• 4148-81-6 1-(1-methyl-2-phenylsulfanyl-ethyl)-benzene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 23275-77-6 1-(1-phenylethyl)-1H-benzo[d][1,2,3]triazole 

Downstream Products

• 83832-34-2 1-((1S,2R)-1-Bromo-2-methoxy-2-phenyl-propyl)-4-methyl-benzene 
• 83832-18-2 1-((1R,2R)-1-Bromo-2-methoxy-2-phenyl-propyl)-4-methyl-benzene 
• 1361148-07-3 1-methyl-2-(4-methylphenyl)-4-phenylnaphthalene 

Relevant academic research and scientific papers

Synthesis of new adamantyl-imine palladium(II) complexes and their application in Mizoroki-Heck and Suzuki-Miyaura C[sbnd]C cross-coupling reactions

Improving carbon–carbon cross-coupling reactions is an ongoing process and finding the most versatile and stable catalyst precursors has been of great interest. Ligand design has been proven to be important since it is responsible for providing electron density and steric saturation around the metal centre, thus contributing towards the stereo-electronic properties. The adamantyl moiety has been used to generate highly bulky and electron-rich ligands for application in palladium-catalysed cross-coupling reactions. Accordingly, we have prepared some Schiff-base adamantyl ligands (L1-L3) and complexed them with [PdCl2(MeCN)2] to afford the (pre)catalysts C1-C3, which were successfully applied in Mizoroki-Heck and Suzuki-Miyaura carbon–carbon cross-coupling reactions. The cross-coupling reaction products were obtained in good yields using 0.5 mol % Pd catalyst loading. C2 and C3 showed remarkable activity in the Mizoroki-Heck coupling reactions involving substrates with substituents on the olefin and aryl halide (including 4-Cl, 4-CH3, -CO2Me and -CO2Et). We also, observed that the Suzuki-Miyaura cross-coupling system was active towards challenging activated and deactivated aryl chlorides, with to up 70% conversions recorded. The mercury poisoning tests conducted revealed that the catalysts act as homogenous molecular active species in the Mizoroki-Heck reactions and act as both homogenous and heterogeneous catalysts in the Suzuki-Miyaura cross-coupling reactions.

Palladium-Catalyzed Mizoroki-Heck Reaction of Nitroarenes and Styrene Derivatives

We have developed a Mizoroki-Heck reaction of nitroarenes with alkenes under palladium catalysis. The use of a Pd/BrettPhos catalyst promoted the alkenylation, whereas other catalysts led to a decrease in the product yield. In addition to nitroarenes, nitroheteroarenes were also applicable to the present reaction. The combination of a nucleophilic aromatic substitution (SNAr) with the denitrative alkenylation produced a multifunctionalized arene in a one-pot operation.

Highly E-Selective, Stereoconvergent Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkenyl Ethers

An improved method for the nickel-catalyzed Suzuki-Miyaura cross-coupling of alkenyl ethers is reported. This stereoconvergent protocol allows for the utilization of a wide range of alkenyl ethers and aryl boronic esters for the synthesis of variously sub

A simple, phosphine free, reusable Pd(ii)-2,2′-dihydroxybenzophenone-SBA-15 catalyst for arylation and hydrogenation reactions of alkenes

An efficient, simple, phosphine and co-catalyst free C-C coupling reaction heterogeneous catalyst via a post grafting method is developed and reported. A covalently anchored phosphine free Pd(ii) based 2,2′-dihydroxybenzophenone (DHBP) complex over organofunctionalized SBA-15 has been synthesized by the reaction between aminofunctionalized SBA-15 (NH2SBA-15) and a 2,2′-dihydroxybenzophenone (DHBP) ligand, and further complexation with Pd(ii)Cl2 to get Pd(ii)-DHBP@SBA-15. The synthesized catalysts were characterized by elemental analysis, XRD, N2 sorption analyses, TG, DTA, FT-IR, solid state 13C and 29Si NMR spectra, XPS, UV-Visible, SEM, EDAX and TEM. The synthesized catalysts were screened in arylation (Heck reactions) and hydrogenation reactions of alkenes, and the results show that Pd(ii)-DHBP@SBA-15 exhibits high conversion and selectivity towards arylation and hydrogenation reactions of alkenes with high stability. The anchored solid catalysts can be recycled effectively and reused several times without major loss in activity.

Room-temperature and transition-metal-free Mizoroki-Heck-type reaction. Synthesis of E-stilbenes by photoinduced C-H functionalization

We report a conceptually different approach toward E-stilbene syntheses by photoinduced direct C-H arylation of alkenes at rt without the addition of transition metals, with a broad range of aryl halides, including ArI, ArBr, and even ArCl. This is the first time that this reaction has been produced without extra solvent but with 18-crown-6 ether and t-BuOK in only 15 min of reaction.

An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes

An operationally simple and practical protocol for the synthesis of (E)-α-halo vinyl sulfides has been achieved via a highly regio- and stereoselective hydrohalogenation of alkynyl thioethers using lithium halides in HOAc or propionic acid at room temperature. It permits the formation of (E)-α-chloro and (E)-α-bromo vinyl sulfides in satisfactory yields with good to excellent stereoselectivities. Moreover, this work results in a new method for the assembly of stereodefined (E)- or (Z)-trisubstituted alkenes featuring the first coupling of the C-X bond of (E)-α-halo vinyl sulfides followed by a subsequent Ni-catalyzed coupling of the C-S bond with Grignard reagents. The Royal Society of Chemistry 2013.

Iron-catalysed tandem cross-dehydrogenative coupling (CDC) of terminal allylic C(sp3) to C(sp2) of styrene and benzoannulation in the synthesis of polysubstituted naphthalenes

A novel iron-catalysed tandem cross-dehydrogenative coupling and benzoannulation process was developed for the synthesis of biologically and synthetically important polysubstituted naphthalene derivatives from simple 1,2-aryl-propenes and styrenes in moderate to good yields. The Royal Society of Chemistry 2012.

Biopolymer-metal complex wool-Pd as a highly active heterogeneous catalyst for Heck reaction in aqueous media

Heterogeneous palladium catalysts, a biopolymer complex wool-Pd, have been applied in water-mediated coupling reactions of aryl bromides without assistance of any phosphine ligands. The catalyst was characterized by XPS, ICP. The results showed that aryl bromides could carry out the coupling reaction with a variety of alkenes at 80 °C, in aqueous media under atmospheric condition. More importantly, the cheap catalyst is stable, which shows negligible metal leaching, and retain good activity for at least ten successive runs without any additional activation treatment. This approach would be very useful from a practical viewpoint.

Nickel-catalyzed alkenylative cross-coupling reaction of alkyl sulfides

A novel cross-coupling reaction of alkyl aryl sulfides with aryl Grignard reagents has been achieved to produce the alkenyl-aryl coupling products in high yields by using catalytic Ni(cod)2 and a bulky N-heterocyclic carbene ligand, SIPr.

Phosphapalladacycle-catalyzed heck reactions for efficient synthesis of trisubstituted olefins: Evidence for palladium(0) intermediates

The coupling reaction of 1,1-disubstituted olefins (α-methyl-styrene, n-butyl methacrylate) with various aryl bromides (Heck reaction) has been studied as a new concept to synthesize trisubstituted olefins. Surprisingly, the nature of the base dramatically influences the product distribution. Thus, a systematic investigation on the role of base in Heck reactions of 1,1-disubstituted olefins was performed. Less coordinating bases like NaOAc, NaOBz or Na2CO3 yield a statistical distribution of regioisomers with the terminal olefin 10 as the major product. However, by using amines like Bu3N or diisopropylethylamine (DIPEA) as base internal olefins can be synthesized with high selectivities. With phosphapalladacycle 3 as catalyst precursor, we were able to obtain catalyst turnover numbers up to 1000, while Pd(OAc)2/2PPh3 was one order of magnitude less active. Analysis of the reaction profile by kinetic investigations led to the postulation of a reduction and subsequent oxidative addition of the catalyst precursor 3 to form 12 as catalytically active intermediate.