Heterobidentate imidazo[1,5-a]pyridine and imidazo[1,5-a]quinoline n-heterocyclic carbene (nhc) ligands, catalyst complexes thereof, and methods using same

A compound of formula (II) selected from the group consisting of:

• wherein:
• M is a transition metal;
• L is a ligand of M, wherein each occurrence of L can be the same or different;
• each occurrence of is a single or double bond,
• wherein no more than bonding a C atom and a N atom is a double bond;
• T1 is N or CRa1;
• T2 is N or CRa2;
• T3 is N or CRa3;
• X is a counter anion;
• Y1, if present, is selected from the group consisting of ORb1 and N(Rb1)(Rb2);
• Y2, if present, is selected from the group consisting of N(Rb1)(Rb2) and optionally substituted phenyl;
• Z is selected from the group consisting of optionally substituted C6-C10 aryl and optionally substituted C2-C8 heteroaryl,
• wherein each optional substituent in Z is independently at least one selected from the group consisting of H, halogen, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, CN, NO2, ORA, N(RA)(RB), C(═O)RA, C(═O)N(RA)(RB), C(═O)ORB, N(RA)S(═O)2RB, S(═O)2N(RA), optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C12 heterocyclyl, optionally substituted C2-C6 alkenyl, optionally substituted benzyl, optionally substituted phenyl, and optionally substituted naphthyl,
• wherein the C1-C6 alkyl, C3-C8 cycloalkyl, C2-C12 heterocyclyl, C2-C6 alkenyl, benzyl, phenyl, and naphthyl are each optionally substituted with at least one substituent selected from the group consisting of halogen, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkyl, C2-C6 alkenyl, benzyl, phenyl, and naphthyl, and C2-C12 heterocyclyl;
• Ra1, Ra2, Ra3, Ra5, and Ra6, if present, are each independently selected from the group consisting of H, halogen, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, CN, NO2, ORAN(RA)(RB), C(═O)RA, C(═O)N(RA)(RB), C(═O)ORB, N(RA)S(═O)2RB, S(═O)2N(RA), optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C8 heterocyclyl, optionally substituted C2-C6 alkenyl, optionally substituted benzyl, optionally substituted phenyl, and optionally substituted naphthyl,
• wherein each optional substituent in each of Ra1, Ra2, Ra3, Ra5, and Ra6 is independently selected from the group consisting of halogen, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkyl, C2-C6 alkenyl, benzyl, phenyl, and naphthyl, and C2-C12 heterocyclyl,
• wherein two vicinal substituents selected from the group consisting of Rai Ra2, Ra3, Ra5, and Ra6 may combine with the carbon atoms to which they are bound to form an optionally substituted C5-C12 cycloalkyl, optionally substituted C2-C12 heterocyclyl, or optionally substituted C6-C10 aryl;
• Ra4 is selected from the group consisting of H, C1-C6 alkyl, C6-C10 aryl, and C2-C12 heterocyclyl;
• Rb1 and Rb2 are each independently selected from the group consisting of H, optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C2-C8 heterocyclyl, optionally substituted C2-C6 alkenyl, optionally substituted benzyl, optionally substituted phenyl, and optionally substituted naphthyl,
• wherein Rb1 and Rb2 may combine with the atom to which they are bound to form an optionally substituted C2-C12 heterocyclyl,
• wherein each optional substituent in each of Rb1 and Rb2 is independently selected from the group consisting of halogen, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkyl, C2-C6 alkenyl, benzyl, phenyl, and naphthyl, and C2-C12 heterocyclyl;
• RA and RB are each independently selected from the group consisting of H, C1-C6 alkyl, C1-C3 haloalkyl, C2-C6 alkenyl, benzyl, naphthyl, C4-C10 heteroaryl, and phenyl, wherein each substituent in RA and RB is optionally substituted with at least one substituent selected from the group consisting of CN, NO2, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkyl, and halogen;
• and
• n is an integer which is selected from the group consisting of 0, 1, 2, and 3.