Biaryl ligands for transition metal-catalyzed reactions

A catalyst composition comprising:

• a) organometallic nanoparticles comprising:
• a nanoparticle (NP) catalyst, prepared by a reduction of an iron salt in an organic solvent, wherein the catalyst comprises at least one other metal selected from the group consisting of Pd, Pt, Au, Ni, Co, Cu, Mn, Rh, Ir, Ru and Os or mixtures thereof;
• b) a ligand of the formula A:
• wherein:
• X is selected from —OR1 or —NR′R″ where R′ and R″ is independently selected from the group consisting of H, C1-10alkyl, C3-6cycloalkyl, C6-14aryl and C4-12heteroaryl;
• X′ is selected from —OR3 or —NR′R″ where R′ and R″ is independently selected from the group consisting of H, C1-10alkyl, C3-6cycloalkyl, C6-14aryl and C4-12heteroaryl;
• each R1 and R3 is independently selected from a group consisting of C1-10alkyl, C3-6cycloalkyl, C6-14aryl and C4-12heteroaryl;
• R2 is selected from the group consisting of C1-10alkyl, C3-6cycloalkyl, C6-14aryl and substituted C6-14aryl and C4-12heteroaryl;
• R4 is H or is selected from the group consisting of —OC1-10alkyl, C1-10alkyl, —SR8, —NR8R9, C6-14aryl and C4-12heteroaryl;
• each R5 and R6 is H or R5 and R6 together with the aryl group to which they are attached to form a substituted or unsubstituted aromatic ring or heteroaromatic ring;
• R7 is H or is selected from the group consisting of —OC1-10alkyl, C1-10alkyl, —SR8, —NR8R9, C6-14aryl and C4-12heteroaryl;
• and
• each R8 and R9 is independently H or C1-10alkyl;
• c) a surfactant;
• and
• d) a reaction solvent or a reaction medium;
• wherein the metal or mixtures thereof is present in less than or equal to 50,000 ppm relative to the iron salt.

An aqueous micellar composition for enabling cross-coupling reactions containing organometallic nanoparticles (NPs) as catalyst, comprising:

• a) an element selected from the group consisting of Fe, C, H, O, Mg, and a halide, or the entire combination thereof;
• and
• b) palladium, or at least one other metal selected from the group consisting of Pt, Au, Ni, Co, Cu and Mn, or a mixture thereof;
• wherein the catalyst (NPs) is prepared from a reduction of an iron salt in a solvent and in the presence of a ligand using a reducing agent;
• wherein the ligand is of the formula A:
• wherein:
• X is selected from —OR1 or —NR′R″ where R′ and R″ is independently selected from the group consisting of H, C1-10alkyl, C3-6cycloalkyl, C6-14aryl and C4-12heteroaryl;
• X′ is selected from —OR3 or —NR′R″ where R′ and R″ is independently selected from the group consisting of H, C1-10alkyl, C3-6cycloalkyl, C6-14aryl and C4-12heteroaryl;
• each R1 and R3 is independently selected from a group consisting of C1-10alkyl, C3-6cycloalkyl, C6-14aryl and C4-12heteroaryl;
• R2 is selected from the group consisting of C1-10alkyl, C3-6cycloalkyl, C6-14aryl and substituted C6-14aryl and C4-12heteroaryl;
• R4 is H or is selected from the group consisting of —OC1-10alkyl, C1-10alkyl, C3-6cycloalkyl, —SR8, —NR8R9, C6-14aryl and C4-12heteroaryl;
• each R5 and R6 is H or R5 and R6 together with the aryl group to which they are attached to form a substituted or unsubstituted aromatic ring or heteroaromatic ring;
• R7 is H or is selected from the group consisting of —OC1-10alkyl, C1-10alkyl, —SR8, —NR8R9, C6-14aryl and C4-12heteroaryl;
• and
• each R8 and R9 is independently H or C1-10alkyl.