Process for producing aromatic compound, and palladium complex

A process for producing an aromatic compound comprising a step of reacting a compound represented by the formula (A) with a compound represented by the formula (B) in the presence of a palladium complex represented by the formula (C) or the formula (C′) and a base:

• Ar1X1)m (A)
• wherein,
• X1 represents a group represented by any one of the formula (1) to the formula (12), M represents a group I element, m is 1 or 2, and when a plurality of X1 are present, the plurality of X1 may be the same or different,
• when m is 1 or 2, Ar1 represents an aryl group having 6 to 36 carbon atoms and optionally having a substituent, or a heteroaryl group having 4 to 36 carbon atoms and optionally having a substituent;
• when m is 1, Ar1 represents an arylene group having 6 to 36 carbon atoms and optionally having a substituent, or a heteroarylene group having 4 to 36 carbon atoms and optionally having a substituent;
• when m is 2, the number of carbon atoms of these groups does not include the number of carbon atoms of the substituent, the optional substituent is selected from Group 1, the aryl group may be a monovalent group formed by directly linking two or more monocyclic and/or condensed-cyclic aryl groups at each occurrence or by indirectly linking two or more monocyclic and/or condensed-cyclic aryl groups via a hetero atom or a carbonyl group at each occurrence,
• the heteroaryl group may be a monovalent group formed by directly linking two or more monocyclic and/or condensed-cyclic heteroaryl groups at each occurrence or by indirectly linking two or more monocyclic and/or condensed-cyclic heteroaryl groups via a hetero atom or a carbonyl group at each occurrence, or may be a monovalent group formed by directly linking at least one monocyclic and/or condensed-cyclic heteroaryl group to at least one monocyclic and/or condensed-cyclic aryl group at each occurrence or by indirectly linking at least one monocyclic and/or condensed-cyclic heteroaryl group to at least one monocyclic and/or condensed-cyclic aryl group via a hetero atom or a carbonyl group at each occurrence,
• the arylene group may be a divalent group formed by directly linking two or more monocyclic and/or condensed-cyclic arylene groups at each occurrence or by indirectly linking two or more monocyclic and/or condensed-cyclic arylene groups via a hetero atom or a carbonyl group at each occurrence and the heteroarylene group may be a divalent group formed by directly linking two or more monocyclic and/or condensed-cyclic heteroarylene groups at each occurrence or by indirectly linking two or more monocyclic and/or condensed-cyclic heteroarylene groups via a hetero atom or a carbonyl group at each occurrence, or may be a divalent group formed by directly linking at least one monocyclic and/or condensed-cyclic heteroarylene group to at least one monocyclic and/or condensed-cyclic arylene group at each occurrence or by indirectly linking at least one monocyclic and/or condensed-cyclic heteroarylene group to at least one monocyclic and/or condensed-cyclic arylene group via a hetero atom or a carbonyl group at each occurrence;
• Group 1:
• 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 heterocycle group optionally having an alkyl group, a group represented by —N(R′)2 wherein two R′ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 of carbon atoms or a heterocycle group optionally having an alkyl group, a group represented by —Si(R′)3 wherein R′ is the same as defined above and three R′ may be the same or different at each occurrence, an acyl group, a group having a carbon atom-nitrogen atom double bond, an acid imide group, an alkoxycarbonyl group, a cycloalkoxycarbonyl group, an aryloxycarbonyl group, a carboxy group, a cyano group, a nitrile group and a nitro group;
• Ar2X2)n (B)
• wherein,
• X2 represents a chlorine atom, a bromine atom, an iodine atom, an alkylsulfonyloxy group, an alkylsulfonyloxy group substituted with a fluorine atom, or an arylsulfonyloxy group, and when a plurality of X2 are present, the plurality of X2 may be the same or different at each occurrence,
• n represents 1 or 2, when n is 1, Ar2 represents an aryl group having 6 to 36 carbon atoms and optionally having a substituent, or a heteroaryl group having 4 to 36 carbon atoms and optionally having a substituent, when n is 2, Ar2 represents an arylene group having 6 to 36 carbon atoms and optionally having a substituent, or a heteroarylene group having 4 to 36 carbon atoms and optionally having a substituent, wherein the number of carbon atoms of these groups does not include the number of carbon atoms of the substituent, the optional substituent is selected from Group 1, the aryl group may be a monovalent group formed by directly linking two or more monocyclic and/or condensed-cyclic aryl groups at each occurrence or by indirectly linking two or more monocyclic and/or condensed-cyclic aryl groups via a hetero atom or a carbonyl group at each occurrence, the heteroaryl group may be a monovalent group formed by directly linking two or more monocyclic and/or condensed-cyclic heteroaryl groups or by indirectly linking two or more monocyclic and/or condensed-cyclic heteroaryl groups via a hetero atom or a carbonyl group at each occurrence, or may be a monovalent group formed by directly linking at least one monocyclic and/or condensed-cyclic heteroaryl group to at least one monocyclic and/or condensed-cyclic aryl group at each occurrence or by indirectly linking at least one monocyclic and/or condensed-cyclic heteroaryl group to at least one monocyclic and/or condensed-cyclic aryl group via a hetero atom or a carbonyl group at each occurrence, the arylene group may be a divalent group formed by directly linking two or more monocyclic and/or condensed-cyclic arylene groups at each occurrence or by indirectly linking two or more monocyclic and/or condensed-cyclic arylene groups via a hetero atom or a carbonyl group at each occurrence, and the heteroarylene group may be a divalent group formed by directly linking two or more monocyclic and/or condensed-cyclic heteroarylene groups at each occurrence or by indirectly linking two or more monocyclic and/or condensed-cyclic heteroarylene groups via a hetero atom or a carbonyl group at each occurrence, or may be a divalent group formed by directly linking at least one monocyclic and/or condensed-cyclic heteroarylene group to at least one monocyclic and/or condensed-cyclic arylene group at each occurrence or by indirectly at least one monocyclic and/or condensed-cyclic heteroarylene group to at least one monocyclic and/or condensed-cyclic arylene group via a hetero atom or a carbonyl group at each occurrence;
• wherein,
• X represents a chlorine atom, a bromine atom or an iodine atom,
• A represents an alkyl group having 1 to 3 carbon atoms,
• R1 represents an alkyl group having a 1 to 20 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms and optionally having a substituent, or a heteroaryl group having 4 to 20 carbon atoms and optionally having a substituent, and R2 and R3 each independently represent an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, wherein the number of carbon atoms of the aryl group and the heteroaryl group does not include the number of carbon atoms of the substituent and the optional substituent is selected from Group 1;
• wherein X, A, R1, R2 and R3 are the same as defined above, and the plurality of X, A, R1, R2 and R3 may be the same or different at each occurrence.

A palladium complex represented by

• the formula (C) or the formula (C′):
• wherein,
• X represents a chlorine atom, a bromine atom or an iodine atom,
• A represents an alkyl group having 1 to 3 carbon atoms,
• R1 represents an alkyl group having to 20 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally having a substituent, or a heteroaryl group having 4 to 20 carbon atoms optionally having a substituent, and R2 and R3 each independently represent an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, wherein the number of carbon atoms of the aryl group and the heteroaryl group does not include the number of carbon atoms of the substituent, and the optional substituent is selected from Group 1;
• Group 1:
• 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 heterocycle group optionally having an alkyl group, a group represented by —N(R′)2 wherein two R′ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms or a heterocycle group optionally having an alkyl group, a group represented by —Si(R′)3 wherein R′ is the same as defined above and three R′ may be the same or different at each occurrence, an acyl group, a group having a carbon atom-nitrogen atom double bond, an acid imide group, an alkoxycarbonyl group, a cycloalkoxycarbonyl group, an aryloxycarbonyl group, a carboxy group, a cyano group, a nitrile group and a nitro group;
• wherein X, A, R1, R2 and R3 represent the same meaning as described above, and a plurality of X, A, R1, R2 and R3 may be the same or different at each occurrence, wherein the complex is a catalyst for Suzuki coupling.