A composition, consisting essentially of copper, a fluoroalkyl group, and a ligand comprising at least one group-V donor. The molar ratio of copper to the fluoroalkyl group is approximately 1.

A composition, consisting essentially of copper, a fluoroalkyl group, and a ligand comprising at least one group-V donor. The molar ratio of copper to the fluoroalkyl group is approximately 1.

A composition, consisting essentially of copper, a fluoroalkyl group, and a ligand comprising at least one group-V donor. The molar ratio of copper to the fluoroalkyl group is approximately 1.

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.

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.

The present invention is directed to providing a method of manufacturing a fluorine-containing compound according to which a fluorine-containing compound is manufactured under a relatively moderate reaction condition by use of a readily available compound. A method of manufacturing a fluorine-containing compound includes reacting a compound having a partial structure expressed by a formula (a) below with a Grignard reagent in the presence of a transition metal compound,

—CF.sub.2—CH.sub.2—L  (a)

wherein L is a sulfonate group.

A method for forming a carbon-carbon bond, wherein a reaction is performed by filling a platinum group metal-supported catalyst into a filling container, and passing a raw material liquid through the platinum group metal-supported catalyst in a continuous circulation manner, and wherein the platinum group metal-supported catalyst is a platinum group metal-supported catalyst in which nanoparticles of a platinum group metal with an average particle diameter of 1 to 100 nm are supported on a non-particulate organic porous ion exchanger formed of a continuous framework phase and a continuous pore phase.

A method for forming a carbon-carbon bond, wherein a reaction is performed by filling a platinum group metal-supported catalyst into a filling container, and passing a raw material liquid through the platinum group metal-supported catalyst in a continuous circulation manner, and wherein the platinum group metal-supported catalyst is a platinum group metal-supported catalyst in which nanoparticles of a platinum group metal with an average particle diameter of 1 to 100 nm are supported on a non-particulate organic porous ion exchanger formed of a continuous framework phase and a continuous pore phase.

A method for forming a carbon-carbon bond, wherein a reaction is performed by filling a platinum group metal-supported catalyst into a filling container, and passing a raw material liquid through the platinum group metal-supported catalyst in a continuous circulation manner, and wherein the platinum group metal-supported catalyst is a platinum group metal-supported catalyst in which nanoparticles of a platinum group metal with an average particle diameter of 1 to 100 nm are supported on a non-particulate organic porous ion exchanger formed of a continuous framework phase and a continuous pore phase.

A method for producing an organometallic nucleophile includes reacting an organohalide and a metal or metal compound with each other by a mechanochemical process in the presence of an ether compound in an amount of 0.5 to 10.0 equivalents relative to 1 equivalent of the organohalide. By utilizing the method, a method for producing an organometallic nucleophile can be performed without using a large-scale apparatus, a reaction method for reactions between an organometallic nucleophile and various organic electrophiles can be performed by an efficient and simplified means, and a simplified method for producing an organometallic nucleophile can be performed with high reactivity.