Disclosed are compounds of Formula I, including all stereoisomers and salts thereof, ##STR00001##
wherein Q.sup.1, Q.sup.2 and R are as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula I, comprising contacting a compound of Formula II ##STR00002## with a compound of Formula III ##STR00003## optionally in the presence of a catalyst or a base to form a compound of Formula I. Further disclosed is a method for preparing a compound of Formula IV, ##STR00004##
comprising reductively cyclizing a compound of Formula I in the presence of a reducing agent.

Disclosed are compounds of Formula I, including all stereoisomers and salts thereof, ##STR00001##
wherein Q.sup.1, Q.sup.2 and R are as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula I, comprising contacting a compound of Formula II ##STR00002## with a compound of Formula III ##STR00003## optionally in the presence of a catalyst or a base to form a compound of Formula I. Further disclosed is a method for preparing a compound of Formula IV, ##STR00004##
comprising reductively cyclizing a compound of Formula I in the presence of a reducing agent.

The present application discloses novel PWNN and PWNWP metal catalysts for organic chemical syntheses including hydrogenation (reduction) of unsaturated compounds or dehydrogenation of substrates. The range of hydrogenation substrate compounds includes esters, lactones, enals, enones, enolates, oils and fats, resulting in alcohols, enols, diols, and triols as reaction products. The catalysts of current application can be used to catalyze a hydrogenation reaction under solvent free conditions. The present catalysts also allow the hydrogenation to proceed without added base, and it can be used in place of the conventional reduction methods employing hydrides of the main-group elements. Furthermore, the catalysts of the present application can catalyze a dehydrogenation reaction under homogenous and/or acceptorless conditions. As such, the catalysts provided herein can be useful in substantially reducing cost and improving the environmental profile of manufacturing processes for a variety of chemicals.

The present application discloses novel PWNN and PWNWP metal catalysts for organic chemical syntheses including hydrogenation (reduction) of unsaturated compounds or dehydrogenation of substrates. The range of hydrogenation substrate compounds includes esters, lactones, enals, enones, enolates, oils and fats, resulting in alcohols, enols, diols, and triols as reaction products. The catalysts of current application can be used to catalyze a hydrogenation reaction under solvent free conditions. The present catalysts also allow the hydrogenation to proceed without added base, and it can be used in place of the conventional reduction methods employing hydrides of the main-group elements. Furthermore, the catalysts of the present application can catalyze a dehydrogenation reaction under homogenous and/or acceptorless conditions. As such, the catalysts provided herein can be useful in substantially reducing cost and improving the environmental profile of manufacturing processes for a variety of chemicals.

Ethylene glycol is prepared from a carbohydrate source by reaction of the carbohydrate source with hydrogen in a continuous process, wherein hydrogen, the carbohydrate source and a liquid diluent are continuously fed into a continuous stirred tank reactor wherein a catalyst system is present, which catalyst system comprises a tungsten compound and at least one hydrogenolysis metal selected from the groups 8, 9 or 10 of the Periodic Table of the Elements, to achieve the reaction between the carbohydrate source and hydrogen to ethylene glycol; wherein continuously a product mixture comprising ethylene glycol and diluent is removed from the continuous stirred tank reactor; and wherein continuously or periodically further at least a tungsten compound is added to the continuous stirred tank reactor (CSTR).

Ethylene glycol is prepared from a carbohydrate source by reaction of the carbohydrate source with hydrogen in a continuous process, wherein hydrogen, the carbohydrate source and a liquid diluent are continuously fed into a continuous stirred tank reactor wherein a catalyst system is present, which catalyst system comprises a tungsten compound and at least one hydrogenolysis metal selected from the groups 8, 9 or 10 of the Periodic Table of the Elements, to achieve the reaction between the carbohydrate source and hydrogen to ethylene glycol; wherein continuously a product mixture comprising ethylene glycol and diluent is removed from the continuous stirred tank reactor; and wherein continuously or periodically further at least a tungsten compound is added to the continuous stirred tank reactor (CSTR).

The present invention relates to a method for reducing unsaturated organic compounds chosen from the group formed by the aldehydes, the ketones, the imines, the carboxylic acids, the amides, and the esters with a boron formate having the formula (I) in the presence of a solvent and optionally a base.

The invention also relates to the use of the method for reducing unsaturated organic compounds chosen from the group formed by the aldehydes, the ketones, the imines, the carboxylic acids, the amides, and the esters according to the invention in the preparation of methanol, methylated amines, formaldehyde and alcohols; for the preparation of reactants for Suzuki coupling reactions; and in the manufacturing of vitamins, pharmaceutical products, glues, acrylic fibres, synthetic leather, pesticides.

The present invention relates to a method for reducing unsaturated organic compounds chosen from the group formed by the aldehydes, the ketones, the imines, the carboxylic acids, the amides, and the esters with a boron formate having the formula (I) in the presence of a solvent and optionally a base.

The invention also relates to the use of the method for reducing unsaturated organic compounds chosen from the group formed by the aldehydes, the ketones, the imines, the carboxylic acids, the amides, and the esters according to the invention in the preparation of methanol, methylated amines, formaldehyde and alcohols; for the preparation of reactants for Suzuki coupling reactions; and in the manufacturing of vitamins, pharmaceutical products, glues, acrylic fibres, synthetic leather, pesticides.

Various embodiments disclosed relate to a method of preparing aryl fluorinated ether compounds. The method involves contacting an aryl halide with a fluorinated alcohol in the presence of a photocatalyst, a base, and irradiation with electromagnetic radiation comprising a wavelength between about 200 nm and about 800 nm. The present invention also provides a method of late-stage photochemical modification of a biologically active compound, such as drugs or agrochemicals. Fluorinated derivatives of griseofulvin, clofibrate, and 2,4-D methyl ester are described herein.

A method for hydrogenating an ester of the general formula (III)

##STR00001## with molecular hydrogen to give the alcohols

##STR00002## at a temperature of 50 to 200? C. and a pressure of 0.1 to 20 MPa abs in the presence of a manganese(I) complex, in which the manganese complex comprises a tridentate ligand L with the general formula (II)

##STR00003## and comprises at least two carbonyl ligands.