Ylide-functionalised phosphanes for use in metal complexes and homogeneous catalysis

A process for performing a coupling reaction containing the steps of

• providing a reaction mixture containing at least a substrate, a coupling partner, and a metal complex containing a phosphane ligands of formulas YPR1R2 (I), Y2PR1 (II) or Y3P (III)
• where
• Y represents an ylide substituent bound to the phosphorus atom through the carbanionic center and having onium groups On and X groups,
• On, independently of the onium groups in other ylide substituents, is selected from phosphonium groups —P(R3R4R5), ammonium groups —N(R3R4R5), sulfoxonium groups —SOR3R4 and sulfonium groups —S(R3R4),
• X, independently of the X groups in other ylide substituents, is selected from hydrogen, alkyl, aryl, alkenyl and heteroaryl groups that may be unsubstituted or substituted with functional groups, silyl (—SiR3R4R5), sulfonyl (—SO2R3), phosphoryl (—P(O)R3R4, —P(S)R3R4, —P(NR3)R4R52), cyano (—CN), alkoxy (—OR3) and amino (—NR3R4) groups, and
• R1, R2, R3, R4 and R5, if any, are independently selected from alkyl, aryl and heteroaryl groups that may be unsubstituted or substituted with functional groups, with the proviso that R1 and R2 are not methyl if X is hydrogen or trimethylsilyl and Z is trimethylphosphonium, or that R1 and R2 are not phenyl if X is p-toluylsulfonyl (—SO2(p-toluyl)) and Z is triphenylphosphonium;
• and
• reacting said substrate with said coupling partner in the presence of the metal complex or its derivative to form a coupling product.

A method for synthesizing a metal complex comprising:

• providing a phosphane ligand of a formula YPR1R2 (I), Y2PR1 (II) or Y3P (III)
• where
• Y represents an ylide substituent bound to the phosphorus atom through the carbanionic center and having onium groups On and X groups,
• On, independently of the onium groups in other ylide substituents, is selected from phosphonium groups —P(R3R4R5), ammonium groups —N(R3R4R5), sulfoxonium groups —SOR3R4 and sulfonium groups —S(R3R4),
• X, independently of the X groups in other ylide substituents, is selected from hydrogen, alkyl, aryl, alkenyl and heteroaryl groups that may be unsubstituted or substituted with functional groups, silyl (—SiR3R4R5), sulfonyl (—SO2R3), phosphoryl (—P(O)R3R4, —P(S)R3R4, —P(NR3)R4R52), cyano (—CN), alkoxy (—OR3) and amino (—NR3R4) groups, and
• R1, R2, R3, R4 and R5, if any, are independently selected from alkyl, aryl and heteroaryl groups that may be unsubstituted or substituted with functional groups, with the proviso that R1 and R2 are not methyl if X is hydrogen or trimethylsilyl and Z is trimethylphosphonium, or that R1 and R2 are not phenyl if X is p-toluylsulfonyl (—SO2(p-toluyl)) and Z is triphenylphosphonium, reacting the phosphane ligand with a suitable metal salt, optionally in a suitable solvent, and obtaining the metal complex.