Process for Producing Phosphonium Borate Compound, Novel Phosphonium Borate Compound, and Method of Using the Same

A method for carbon-carbon bond forming reactions, carbon-nitrogen bond forming reactions and carbon-oxygen bond forming reactions selected from the group consisting of Suzuki-Miyaura reaction, Kumada-reaction, Negishi reaction, Hiyama reaction, Kosugi-Stille reaction, Heck reaction, Sonogashira reaction, a-arylation of carbonyl compounds, Buchwald-Hartwig amination and ether synthesis wherein a transition metal complex having a phosphine ligand produces catalytic effects, comprising the step of using a phosphonium borate compound in combination with a transition metal, transition metal salt, transition metal oxide or transition metal complex in place of the transition metal complex having a phosphine ligand in the reaction, the phosphonium borate compound being represented by Formula (I):

• (R1)(R2)(R3)PH.BAr4 (I)
• wherein R1 is a primary alkyl group of 1 to 20 carbon atoms, a secondary alkyl group of 3 to 20 carbon atoms, a tertiary alkyl group of 4 to 20 carbon atoms, or a cycloalkyl group of 3 to 20 carbon atoms;
• R2 is a hydrogen atom, a primary alkyl group of 1 to 20 carbon atoms, a secondary alkyl group of 3 to 20 carbon atoms, a tertiary alkyl group of 4 to 20 carbon atoms, a cycloalkyl group of 3 to 20 carbon atoms, an aralkyl group of 7 to 20 carbon atoms, or an alkyl group of 3 to 20 carbon atoms;
• R3 is a hydrogen atom, a primary alkyl group of 1 to 20 carbon atoms, a secondary alkyl group of 3 to 20 carbon atoms, a tertiary alkyl group of 4 to 20 carbon atoms, a cycloalkyl group of 3 to 20 carbon atoms, an aryl group of 6 to 30 carbon atoms, an aralkyl group of 7 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, or an alkyl group of 3 to 20 carbon atoms;
• R1, R2 and R3 may be the same or different from one another;
• and
• Ar is an aryl group of 6 to 20 carbon atoms.