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1. A method of producing an aromatic compound, comprising a step of mixing a compound represented by the formula (A): wherein, X1 represents a group represented by the formula (1), (2), (3), (4), (5) or (6): Ar1 represents a monovalent or divalent aromatic hydrocarbon group having a number of carbon atoms of 6 to 36, and m represents 1 or 2, a carbon atom contained in the aromatic hydrocarbon group may be substituted with a hetero atom or a carbonyl group, and a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with a fluorine atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylcycloalkyl group, an arylalkenyl group, an arylalkynyl group, a heterocyclic group which may have a substituent, an amino group which may have a substituent, a silyl group which may have a substituent, an acyl group, a group having a carbon atom-nitrogen atom double bond as a partial structure, an acid imide group, an alkoxycarbonyl group, a cycloalkoxycarbonyl group, an aryloxycarbonyl group, a carboxyl group, a cyano group or a nitro group, and a compound represented by the formula (B): wherein, X2 represents a chlorine atom, a bromine atom, an iodine atom, an alkylsulfonyloxy group, a fluorine-substituted alkylsulfonyloxy group or an arylsulfonyloxy group, Ar2 represents a monovalent or divalent aromatic hydrocarbon group having a number of carbon atoms of 6 to 36, and n represents 1 or 2, a carbon atom contained in the aromatic hydrocarbon group may be substituted with a hetero atom or a carbonyl group, and a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with a fluorine atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylcycloalkyl group, an arylalkenyl group, an arylalkynyl group, a heterocyclic group which may have a substituent, an amino group which may have a substituent, a silyl group which may have a substituent, an acyl group, a group having a carbon atom-nitrogen atom double bond as a partial structure, an acid imide group, an alkoxycarbonyl group, a cycloalkoxycarbonyl group, an aryloxycarbonyl group, a carboxyl group, a cyano group or a nitro group, in the presence of at least one phosphine compound selected from the group consisting of a phosphine represented by the formula (C): wherein, A1 and A2 represent each independently a cyclopentyl group which may have a substituent, R1 and R5 represent each independently a hydrogen atom, a fluorine atom, an alkyl group having a number of carbon atoms of 2 to 20, a cycloalkyl group having a number of carbon atoms of 3 to 20, a fluoroalkyl group having a number of carbon atoms of 1 to 20, an alkoxy group having a number of carbon atoms of 1 to 20, a cycloalkoxy group having a number of carbon atoms of 3 to 20, a fluoroalkoxy group having a number of carbon atoms of 1 to 20, an aryl group having a number of carbon atoms of 6 to 20, an aryloxy group having a number of carbon atoms of 6 to 20, a group represented by the formula (D): wherein, R6 represents a hydrogen atom, an alkyl group having a number of carbon atoms of 1 to 20 or a cycloalkyl group having a number of carbon atoms of 3 to 20, R7 and R8 represent each independently an alkyl group having a number of carbon atoms of 1 to 20 or a cycloalkyl group having a number of carbon atoms of 3 to 20, and R7 and R8 may be linked to form a ring, or a group represented by the formula (E): wherein, R9, R10, R11 and R12 represent each independently a hydrogen atom, an alkyl group having a number of carbon atoms of 1 to 20, a cycloalkyl group having a number of carbon atoms of 3 to 20 or an aryl group having a number of carbon atoms of 6 to 20, R2, R3 and R4 represent each independently a hydrogen atom, a fluorine atom, an alkyl group having a number of carbon atoms of 1 to 20, a cycloalkyl group having a number of carbon atoms of 3 to 20, a fluoroalkyl group having a number of carbon atoms of 1 to 20, an alkoxy group having a number of carbon atoms of 1 to 20, a cycloalkoxy group having a number of carbon atoms of 3 to 20, a fluoroalkoxy group having a number of carbon atoms of 1 to 20, an aryl group having a number of carbon atoms of 6 to 20 or an aryloxy group having a number of carbon atoms of 6 to 20, here, all of R1 to R5 do not simultaneously represent a hydrogen atom, and, when at least one of R1 to R5 is a fluoroalkyl group having a number of carbon atoms of 1 to 20, at least one of the remaining R1 to R5 is not a hydrogen atom or a fluoroalkyl group having a number of carbon atoms of 1 to 20, further, R2 and R3 may be linked to form a ring together with a carbon atom to which they are linked, and R3 and R4 may be linked to form a ring together with a carbon atom to which they are linked, and a phosphonium salt represented by the formula (F): wherein, A1, A2, R1 to R5 represent the same meaning as described above, and Z represents an anion; a base, a palladium compound and an aprotic organic solvent. |
