Method for producing phosphinobenzene borane derivative, method for producing 1,2-bis(dialkylphosphino)benzene derivative, and transition metal complex

A method for producing a 1,2-bis(dialkylphosphino)benzene derivative, the method comprising:

• a reaction step (A) of:
• obtaining liquid A comprising a 1,2-dihalogenobenzene represented by the following general formula (1):
• wherein X denotes a halogen atom;
• R1 denotes a monovalent substituent;
• and n denotes an integer of 0 to 4;
• obtaining liquid B comprising a phosphine borane compound obtained by deprotonating a hydrogen-phosphine borane compound represented by the following general formula (2):
• wherein R2 and R3 each denote a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms which may be substituted, a cycloalkyl group which may be substituted, or a phenyl group which may be substituted;
• and R2 and R3 may be the same or different;
• and
• then adding the liquid B to the liquid A to be allowed to react to thereby obtain a phosphinobenzene borane derivative represented by the following general formula (3):
• wherein R1, R2, R3, X and n have the same meanings as defined above;
• and
• the following reaction step (B1), reaction step (B2) or reaction step (B3) of obtaining the 1,2-bis(dialkylphosphino)benzene derivative represented by the following general formula (6):
• wherein R1, R2, R3, X and n have the same meanings as defined above;
• and R4 and R5 each denote a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms which may be substituted, a cycloalkyl group which may be substituted, or a phenyl group which may be substituted;
• and R4 and R5 may be the same or different
• by carrying out the reaction step (B1), the reaction step (B2) or the reaction step (B3):
• the reaction step (B1):
• a step of deboranating the phosphinobenzene borane derivative represented by the general formula (3), then lithiating the resultant, then reacting the resultant with an alkyldihalogenophosphine represented by the general formula (4):
• RaPX12 (4)
• wherein Ra is one of R4 and R5 in the general formula (6);
• and X1 denotes a halogen atom, and then reacting the resultant with a Grignard reagent represented by the general formula (5):
• RbMgX2 (5)
• wherein Rb is the other of R4 and R5 in the general formula (6);
• and X2 denotes a halogen atom;
• the reaction step (B2):
• a step of deboranating the phosphinobenzene borane derivative represented by the general formula (3), then lithiating the resultant, then reacting the resultant with a dialkylhalogenophosphine represented by the general formula (4′):
• Rc2PX3 (4′)
• wherein Rc is a group equivalent to R4 and R5 in the case of being the same in the general formula (6);
• and X3 denotes a halogen atom:
• the reaction step (B3):
• a step of lithiating the phosphinobenzene borane derivative represented by the general formula (3), then reacting the resultant with a dialkylhalogenophosphine represented by the general formula (4′):
• Rc2PX3 (4′)
• wherein Rc is a group equivalent to R4 and R5 in the case of being the same in the general formula (6);
• and X3 denotes a halogen atom, and then deboranating the resultant.