Lewis acidic metal-organic framework (MOF) materials comprising triflate-coordinated metal nodes are described. The materials can be used as heterogenous catalysts in a wide range of organic group transformations, including Diels-Alder reactions, epoxide-ring opening reactions, Friedel-Crafts acylation reactions and alkene hydroalkoxylation reactions. The MOFs can also be prepared with metallated organic bridging ligands to provide heterogenous catalysts for tandem reactions and/or prepared as composites with support particles for use in columns of continuous flow reactor systems. Methods of preparing and using the MOF materials and their composites are also described.

A method for synthesizing a chiral -hydroxy acid ester compound is disclosed. The method includes the steps of: using an aldehyde compound and a monoalkyl malonate as raw materials, using a metal and a chiral ligand as a catalyst to make the raw materials be directly and fully reacted in an organic solvent and form a reaction solution, and separating and purifying the reaction solution to obtain the highly stereoselective -hydroxy acid ester compound. The beneficial effects are mainly embodied in: 1. simple operation; 2. rapidly constructing a highly stereoselective -hydroxy acid ester skeleton structure molecule; 3. high reaction yield and good stereoselectivity. Therefore, the invention has high basic research significance, industrial production value and social economic benefit.

This application pertains to amine-functionalized polymers by ring-opening metathesis (ROMP) of amine functionalized cycloalkenes.

The invention relates to ylide-functionalized phosphane ligands, the production of same and use in transition metal compounds, as well as the use of same as catalysts in organic reactions.

Disclosed is a method for preparing a 1,3-dicarbonyl compound based on a metal hydride/palladium compound system. The method includes the following steps: suspending a palladium compound and a metal hydride in a solvent under the protection of nitrogen, then adding an electron-deficient olefin compound, reacting same at 0 C.-100 C. for 0.3 to 10 hours, then adding a saturated ammonium chloride aqueous solution to stop the reaction, and then subjecting same to extraction, evaporation until dryness, and column chromatography purification to obtain the 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used by the present invention are reagents easily obtained in a laboratory. Compared to a common hydrogen hydrogenation method, the method is easier to operate, and has a higher safety, mild conditions, and a high reaction yield.

In one aspect, phosphine compounds comprising three adamantyl moieties (PAd.sub.3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd.sub.3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

Provided is a one-pot process for preparing propionic acid, which comprises (i) treating ethylene with a C.sub.1-C.sub.6 alkanol, water, and carbon monoxide in the presence of a catalyst system comprising the reaction product of (a) a Group 8 to 10 transition metal compound such as a palladium or ruthenium compound; and (b) an activating anion, at elevated temperature and pressure. The process also provides a facile, continuous process for the preparation of propionic acid via the alkoxycarbonylation of ethylene at elevated temperature and pressure followed by hydrolysis, in one reaction vessel.

A method for producing a compound represented by formula (4)

##STR00001##

[R.sup.1-R.sup.5 represent hydrogen atoms, formula (2), or formula (5), and at least one of R.sup.1-R.sup.5 is a group represented by formula (5) (Ar.sup.1Ar.sup.3 are the same as below)],

##STR00002##

the method comprising carrying out deprotection after reacting an amine compound represented by formula (1)

##STR00003##

[R.sup.1-R.sup.5 each independently represent a hydrogen atom or a group represented by formula (2)

##STR00004##

(Ar.sup.1 and Ar.sup.2 represent aryl groups and Ar.sup.3 represents an arylene group, and any two of Ar.sup.1-Ar.sup.3 may bond to form a ring), and at least one of R.sup.1-R.sup.5 is a hydrogen atom] with a compound represented by formula (3)

##STR00005##

(X represents a halogen atom, etc., and R.sup.6-R.sup.8 represent an alkyl group, etc.) in the presence of a catalyst and a base, is a method for producing an aniline derivative suited to efficient industrial production that does not require a large excess of base and oxygen in the process of deprotection.

Methods for preparing the Bruton's Tyrosine Kinase (BTK) inhibitor compound 2-{3-hydroxymethyl-1-methyl-5-[5-((S)-2-methyl-4-oxetan-3-yl-piperazin-1-yl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-[3,4]bipyridinyl-2-yl}-7,7-dimethyl-3,4,7,8-tetrahydro-2H,6H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one are provided. Methods for preparing tricyclic lactam compounds are also provided.

Provided herein are palladium (Pd) catalysts with improved performance in biological environments. In particular, formulations, methods of preparations, and storage conditions are provided that provide improved performance of Pd catalysts under protein-rich conditions.