Process for Production of 2-(Substituted Phenyl)-3,3,3-Trifluoropropene Compound

A process for production of a 2-(substituted phenyl)-3,3,3-trifluoropropene compound or salt thereof, the compound being represented by the formula (7):

• wherein X represents a halogen atom, a cyano group, a nitro group, —SF5, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a hydroxy (C1-C6)haloalkyl group, a C1-C6 alkoxy(C1-C6)haloalkyl group, a C1-C6 haloalkoxy(C1-C6)haloalkyl group, a C3-C8 halocycloalkyl group, —OR3, —OSO2R3 or —S(O)rR3;
• and m represents an integer of 1 to 5 and when m represents 2 or more, each of Xs may be identical to or different from each other,
• by reacting a substituted phenylboronic acid or a substituted phenylboronic ester or a substituted phenylboronic acid salt represented by the formula (1):
• wherein X and m represent the same meanings as those above described;
• R1 and R2 may be identical to or different from each other and represent a hydrogen atom or an alkyl group, or a divalent hydrocarbon residue formed by R1 and R2 together in which the terminals of R1 and R2 are bonded to each other;
• R3 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C3 haloalkoxy (C1-C3)haloalkyl group;
• and
• r represents an integer of 0 to 2, with a 2-halogen-3,3,3-trifluoropropene compound or salt thereof, the compound being represented by the formula (2):
• wherein Y represents a halogen atom, in the presence of a complex catalyst represented by the formula (3):
• (LaMbGc)n(A)n (3)
• wherein M represents as a central atom, an ion of a metal belonging to Group 10 on the elementary periodic table in an oxidation state number of 1 to 8;
• G represents a unidentate or multidentate charged or uncharged ligand bonded to the central atom M;
• L is bonded as a ligand to the central atom M, and represents a phosphine compound represented by the formula (4):
• wherein each of R4, R5 and R6 may be identical to or different from each other and represent a hydrogen atom, a C1-C6 alkyl group, a C3-C18 monocyclic or polycyclic cycloalkyl group or a C6-C14 aryl group which may be substituted by a substituent such as a di-(C1-C6 alkyl) amino group, a C1-C6 alkoxyl group and an aryl group which may be substituted by a substituent such as a di-(C1-C6 alkyl)amino group and a C1-C6 alkoxyl group, or a carbene represented by the formula (5):
• or by the formula (6):
• wherein each of R7 and R8 may be identical to or different from each other and represent a linear or branched C1-C7 alkyl group, a monocyclic or polycyclic C3-C18 cycloalkyl group or an aryl group having 6 to 14 carbon atoms which may be substituted by a substituent such as a linear or branched C1-C7 alkyl group, or a monocyclic or polycyclic C3-C18 cycloalkyl group;
• each of R9, R10, R11 and R12 may be identical to or different from each other, may be also a hydrogen atom, and represent a linear or branched C1-C7 alkyl group, a monocyclic or polycyclic C3-C18 cycloalkyl group, an aryl group having 6 to 14 carbon atoms which is optionally substituted by a linear or branched C1-C7 alkyl group, a linear or branched C1-C7 alkoxy group, or a linear or branched C1-C7 alkylthio group;
• and
• R7 and R9, R8 and R10, R7, R9 and R11, or R8, R10 and R12may form together a condensed ring,
• wherein when a represents 2 to 15, each of Ls may be identical to or different from each other with proviso that all Ls do not represent simultaneously triphenylphosphine,
• A represents a univalently or multivalently charged anion;
• b represents any integer of 1 to 3;
• a represents an integer produced by multiplying any integer of 1 to 5 by the above integer b;
• c represents 0 or represents an integer produced by multiplying an integer of 1 to 4 by the above b;
• and
• n represents any integer of 1 to 6.