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Relevant academic research and scientific papers

Recyclable cellulose-palladium nanoparticles for clean cross-coupling chemistry

Cheap, recyclable, and robust cellulose-palladium nanoparticles were developed and fully characterized by FTIR, TEM, XPS, TGA, and NMR. The nanoparticles enabled cross-coupling chemistry in a truly general fashion i.e., Suzuki-Miyaura, Heck, Sonogashira, and C-H activation. Notably, all types of transformations were achieved with a single type of nanocatalyst. Complete recyclability of the catalyst and low traces of palladium in the product demonstrates the greenness of the protocol.

A highly active palladium(II)-bis(oxazoline) catalyst for Suzuki-Miyaura, Mizoroki-Heck and sonogashira coupling reactions in aqueous dimethylformamide

An efficient catalytic system based on a new palladium-bis(oxazoline) (Pd-BOX-1) complex has been developed. The complex Pd-BOX-1 adopts a legless chair-type structure where the distorted square planar [PdN2Cl2] moiety and the benzene ring spacer represent the seat and the chair back, respectively. The catalytic activity of Pd-BOX-1 has been investigated in dimethylformamide-water under aerobic and mild conditions in Suzuki-Miyaura coupling reactions of arylboronic acids with aryl iodides, aryl bromides and aryl chlorides, Mizoroki-Heck coupling reactions of aryl halides with styrene derivatives, and Sonogashira coupling reactions of aryl halides with terminal alkynes. A wide range of functional groups as substituents on the arylboronic acids and aryl halides were considered. Pd-BOX-1 demonstrates exceptional air and moisture stability. Of note, the catalyst system based on Pd-BOX-1 shows high recycling ability in Suzuki-Miyaura coupling reactions in dimethylformamide-water without any loss in catalytic activity.

Suzuki-Miyaura coupling of aryl sulfonates with arylboronic acids using a morpholine-Pd(OAc)2 catalyst system

We report a new catalyst system, a morpholine-Pd(OAc)2 complex, for Suzuki-Miyaura coupling of aryl tosylates or mesylates with arylboronic acids to give biaryl compounds. The morpholine-Pd(OAc)2 catalyst system is proposed to be a precursor of the catalytically active species in the coupling reaction. Aryl chlorides and aryl triflates can also be used in this coupling reaction. Altogether, 22 biaryl compounds were obtained using this catalyst system. We report a new catalyst system, a morpholine-Pd(OAc) 2 complex, for Suzuki-Miyaura coupling of aryl tosylates or mesylates with arylboronic acids to give biaryl compounds. The morpholine-Pd(OAc) 2 catalyst system is proposed to be a precursor of the catalytically active species in the coupling reaction. Copyright

Efficient PdCl2-catalyzed Suzuki reactions using simple dicationic imidazolium salts as ligands in aqueous DMF

Three new palladium catalysts, prepared via reactions of PdCl2 with readily obtained and inexpensive dicationic imidazolium salts, have been developed for the Suzuki reaction. The pre-catalyst was formed in situ using the imidazolium ligand, ba

C,N-palladacycles containing N-heterocyclic carbene and azido ligands - Effective catalysts for Suzuki-Miyaura cross-coupling reactions

Azido-palladacycles containing C,N-donor and N-heterocyclic carbene ligands, [(C,N-L)Pd(N3)(NHC)] [NHC = IPr; 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene], were prepared from (i) IPr and dinuclear PdII azides, [Pd(μ-N3)(C,N-Ln)]2 [C,N-L1H = N,N′-dimethylbenzylamine; C,N-L2H = 2-(2′-thienyl)pyridine; C,N-L3H = azobenzene; C,N-L 4H = 2-(p-tolyl)pyridine], or from (ii) NaN3 and mononuclear PdII chloride, [Pd(Cl)(IPr)(C,N-Ln)], in aqueous solution. The structures of two of these products were determined by X-ray crystallography. The palladacycles showed high catalytic efficiency toward activated and nonactivated aryl bromides (at room temperature) as well as aryl chlorides (at 80 C) in Suzuki-Miyaura cross-coupling reactions. In addition, coupling reactions of aryl chlorides using potassium aryl trifluoroborates instead of phenyl boronic acid gave good-to-excellent product yields. Suzuki-Miyaura cross-coupling reactions of aryl bromides and chlorides with organoboronic acid as well as potassium aryl trifluoroborates catalyzed by C,N-donor palladacycles containing N-heterocyclic carbene (NHC) and azido ligands under various conditions have been performed. Copyright

An efficient protocol for the palladium-catalysed Suzuki-Miyaura cross-coupling

The palladacyclic catalyst precursor received by ortho-palladation of ([1,1′-biphenyl]-2-yloxy)diisopropyl-phosphine represents a highly active system for Suzuki-Miyaura cross-coupling reactions when used in neat water. An efficient, broadly applicable and sustainable aqueous protocol was developed using 2.5 eq. of Na2CO3 as base, allowing the reaction to be performed under air and at ambient temperature with Pd loadings of 0.04 mol%. Coupling products are obtained in high yields and excellent purity by simple filtration with no organic solvents needed throughout the whole reaction. A broad variety of functional groups are tolerated and a large number of substrates can be applied with this protocol. The crystal structure of the palladacyclic catalyst precursor is presented as well as investigations targeting the nature of catalyst activation and the active catalytic species.

Assessment and use of two silicon carbide multi-well plates for library synthesis and proteolytic digests using microwave heating

The use of two silicon carbide plates is reported for the preparation of three libraries of organic molecules using microwave heating. In addition, a preliminary study has been carried out, showing that one of the plates can also be used in a proteomics setting. Both the 24-position and 48-position plates heated evenly when irradiated with microwave energy. The 48-position plate was used to prepare a library of N-aryl functionalized β-amino esters via an aza-Michael reaction between anilines and Michael acceptors. The 24-position plate was used to prepare a library of biaryls via a Suzuki coupling methodology and a library of 1,4-dihydropyridines via a Hantzsch synthesis. The 48-position plate was also used to perform the proteolytic digestion of insulin chain B by trypsin. The Royal Society of Chemistry 2009.

Carbon-carbon cross-coupling reactions under continuous flow conditions using poly(vinylpyridine) doped with palladium

Coordinative immobilization of an oxime-based pallada-cycle to poly(vinylpyridine)/glass composite materials shaped as Raschig rings or placed within the PASSflow microreactor affords technical devices that are well suited for performing palladium-catalyzed carbon-carbon cross-coupling reactions in the flow-through mode. Reusability of the immobilized precatalyst as well as applications in the microwave field were investigated. Experiments with thiol- and pyridine-based scavengers were carried out, which revealed that the active palladium species is likely to be composed of nanoparticles of unknown nature and that the poly(vinylpyridine) carrier has scavenging properties for these particles. Georg Thieme Verlag Stuttgart.

Novel inhibitors of 17β-hydroxysteroid dehydrogenase type 1: Templates for design

The 17β-hydroxysteroid dehydrogenases (17β-HSDs) catalyze the interconversion between the oxidized and reduced forms of androgens and estrogens at the 17 position. The 17β-HSD type 1 enzyme (17β-HSD1) catalyzes the reduction of estrone (E1) to estradiol a