An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound. The above object can be achieved by a method for producing a compound represented by formula (1): ##STR00001##
wherein R.sup.1 represents an organic group, R.sup.A represents hydrogen or fluorine, R.sup.4a represents hydrogen or an organic group, R.sup.4b represents hydrogen or an organic group, R.sup.5a represents hydrogen or an organic group, R.sup.5b represents hydrogen or an organic group, and
R.sup.2 represents hydrogen or an organic group; R.sup.2 is optionally connected to R.sup.4a to form a ring; the method comprising step A of reacting a compound represented by formula (2): ##STR00002##
wherein X.sup.1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3): ##STR00003##
wherein X.sup.2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

Provided herein, in part, is a new class of sterically bulky, easily prepared N-heterocyclic carbene (NHC) ligands of Formula I, or a salt, solvate, geometric isomer, or stereoisomer thereof. The ligands are readily synthetically accessible exploiting the cost-effective, modular alkylation of anilines. The NHC ligands of the present disclosure can be used to prepare effective catalysts with transition metals, including the compound of Formula II, or a salt, solvate, geometric isomer, or stereoisomer thereof. In certain embodiments, the transition metal is Pd.

An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound.

The above object can be achieved by a method for producing a compound represented by formula (1):

##STR00001## wherein R.sup.1 represents an organic group, R.sup.A represents hydrogen or fluorine, R.sup.4a represents hydrogen or an organic group, R.sup.4b represents hydrogen or an organic group, R.sup.5a represents hydrogen or an organic group, R.sup.5b represents hydrogen or an organic group, and R.sup.2 represents hydrogen or an organic group; R.sup.2 is optionally connected to R.sup.4a to form a ring; the method comprising step A of reacting a compound represented by formula (2):

##STR00002## wherein X.sup.1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3):

##STR00003## wherein X.sup.2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

The present invention is directed to curable compositions comprising: (a) a polyene; (b) a polythiol, present in an amount greater than 10 percent by weight based on the total weight of components (a) and (b) in the curable composition; and (c) a catalytic component consisting essentially of: (i) a metal compound; and (ii) a compound different from (i) that catalyzes an addition reaction between an ethylenically unsaturated compound and a thiol. The catalytic composition is essentially free of vanadium compounds. In the curable composition, either (1) both components (i) and (ii) of the catalytic composition (c) are added as a single package to (a) and/or (b); or (2) component (i) and/or (ii) of the catalytic composition (c) is added in separate packages to (a) and/or (b) of the curable composition. The present invention is further drawn to coated articles and methods of extending pot life of a curable composition.

This disclosure is directed to: (a) processes for preparing compounds and salts thereof that, inter alia, are useful for inhibiting hepatitis C virus (HCV); (b) intermediates useful for the preparation of the compounds and salts; (c) pharmaceutical compositions comprising the compounds or salts; and (d) methods of use of such compositions.

The present invention discloses a diphenylamine-linked chiral bis(oxazoline) ligand without C.sub.2-symmetry of formula 3 and its synthesis method and application in an asymmetric catalytic reaction, wherein C.sub.2-symmetry is lost by introducing different groups into the diphenylamine backbone to realize precise control of “electronic effect” of the ligand backbone. An anthranilic acid derivative and an orthochlorobenzoic acid derivative are used as starting materials to prepare a compound of formula 1, and then the compound of formula 1 is reacted with a chiral amino alcohol compound to prepare a β-bishydroxy amide compound of formula 2, and the compound of formula 2 is further subjected to condensation to obtain the diphenylamine-linked chiral bis(oxazoline) ligand without C.sub.2-symmetry of formula 3. The present invention also provides an application of a catalyst formed by coordination of the diphenylamine-linked chiral bis(oxazoline) ligand without C.sub.2-symmetry with copper salt, zinc salt, nickel salt, iron salt or rhodium salt, in an asymmetric catalytic reaction.

##STR00001##

The present invention relates to a process for the synthesis of Vortioxetine (I) or a pharmaceutically acceptable salt thereof. This process is accomplished by using a catalytic system consisting of a copper salt and an organic ligand, which can promote the formation of both C—N and C—S bond in one-pot, giving rise to an efficient, simple and industrially viable synthetic route for Vortioxetine.

Various embodiments disclosed relate to a method of oxidizing sulfur-containing compounds. The method involves contacting a sulfur-containing compound with a helmet phthalocyaninato-type catalyst in the presence of an oxidant. The present invention also provides a method of removing undesired sulfur-containing compounds from a fluid, such as natural gas, crude oil or an aqueous waste stream.

An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound. The above object can be achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein R.sup.1 represents an organic group, R.sup.A represents hydrogen or fluorine, R.sup.4a represents hydrogen or an organic group, R.sup.4b represents hydrogen or an organic group, R.sup.5a represents hydrogen or an organic group, R.sup.5b represents hydrogen or an organic group, and R.sup.2 represents hydrogen or an organic group; R.sup.2 is optionally connected to R.sup.4a to form a ring; the method comprising step A of reacting a compound represented by formula (2):

##STR00002##

wherein X.sup.1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3):

##STR00003##

wherein X.sup.2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

The present invention is directed to curable compositions comprising: (a) a polyene; (b) a polythiol, present in an amount greater than 10 percent by weight based on the total weight of components (a) and (b) in the curable composition; and (c) a catalytic component consisting essentially of: (i) a metal compound; and (ii) a compound different from (i) that catalyzes an addition reaction between an ethylenically unsaturated compound and a thiol. The catalytic composition is essentially free of vanadium compounds. In the curable composition, either (1) both components (i) and (ii) of the catalytic composition (c) are added as a single package to (a) and/or (b); or (2) component (i) and/or (ii) of the catalytic composition (c) is added in separate packages to (a) and/or (b) of the curable composition. The present invention is further drawn to coated articles and methods of extending pot life of a curable composition.