The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent expressed as a 3-methyl-3-butenyl M of General Formula (8):

##STR00001##

wherein M is a cationic moiety, with an acetal compound of General Formula (9):

##STR00002##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent expressed as a 3-methyl-3-butenyl M of General Formula (8):

##STR00001##

wherein M is a cationic moiety, with an acetal compound of General Formula (9):

##STR00002##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.

Shown and described are improved processes for the preparation of dapagliflozin of Formula I, ##STR00001##
or its solvates or co-crystals thereof and intermediates and their use in the preparation of dapagliflozin of Formula I or its solvates or co-crystals thereof.

Shown and described are improved processes for the preparation of dapagliflozin of Formula I, ##STR00001##
or its solvates or co-crystals thereof and intermediates and their use in the preparation of dapagliflozin of Formula I or its solvates or co-crystals thereof.

An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.

An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.

An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.

A more environmentally friendly synthesis method of 4-bromo-2-(4′-ethoxyphenyl)-1-chlorobenzene with simplified steps provides a more effective synthetic strategy for producing key intermediates of SGLT-2 inhibitors such as dapagliflozin, sotagliflozin, and ertugliflozin. In the presence of trifluoroacetic anhydride, 5-bromo-2-chlorobenzoic acid and phenetole are selected to complete a direct acylation reaction under the catalysis of boron trifluoride diethyl etherate, and triethylsilane is added thereinto without treatment for one-pot reaction to obtain a target compound 4-bromo-2-(4′-ethoxyphenyl)-1-chlorobenzene.

Disclosed is a cross-coupling reaction method which forms a chemical bond selected from C—N, C—B, C—C, C—O and C—S bonds, the method comprising: preparing an aromatic compound (1) having a leaving group; preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic amino compound (2-1), a diboronic acid ester or the like (2-2), an aromatic boronic acid or the like (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; and performing a cross-coupling reaction of the compound (1) with the compound (2) in the presence of a palladium catalyst, a base and a compound (4) having a carbon-carbon double bond or a carbon-carbon triple bond, in the absence of a solvent.