A tautomeric ligand enables biomimetic c-h hydroxylation with molecular oxygen

A process for making a compound of formula (2):

• comprising contacting a compound of formula (1):
• with a source of Pd(II) in the presence of O2 and a ligand of formula (L):
• whereby the compound of formula (2) is formed, wherein:
• is a C6-C10-aryl or 5-10-membered heteroaryl (wherein 1-4 heteroaryl ring members are independently selected from the group consisting of O, S, and N) that is optionally further fused to one or two rings independently selected from C6-C10-aryl, 5-10-membered heteroaryl (wherein 1-4 heteroaryl ring members are independently selected from the group consisting of O, S, and N), C3-C14-cycloalkyl, 3- to 14-membered heterocycloalkyl (wherein 1-4 heterocycloalkyl ring members are independently selected from N, O, and S), and fused combinations thereof, wherein
• each ring in
• is independently and optionally substituted with one to four substituents selected from the group consisting of —CN, halo, oxo, NRARB, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, —C(O)H, C(O)C1-C6-alkyl, C(O)NRARB, S(O)NRARB, S(O)2NRARB, C3-C14-cycloalkyl, C6-C10-aryl, C6-C10-aryloxy, 3- to 14-membered heterocycloalkyl and —(C1-C6-alkyl)-(3- to 14-membered heterocycloalkyl) (wherein 1-4 ring members are independently selected from N, O, and S), and 5- to 10-membered heteroaryl (wherein 1-4 heteroaryl members are independently selected from N, O, and S), wherein
• each alkyl, aryl, cycloalkyl, heterocycloalkyl, and heteroaryl moiety is optionally substituted with one to four substituents selected from the group consisting of halo, oxo, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C(O)NRARB, C1-C6-alkoxy, C6-C10-aryl (optionally substituted by one to three halo and C1-C6-alkyl), and 5- to 10-membered heteroaryl (wherein 1-4 heteroaryl members are independently selected from N, O, and S;
• optionally substituted by one to three substituents selected from C1-C6-alkyl and 5- to 10-membered heteroaryl);
• RA and RB are independently selected from the group consisting of H, C1-C6-alkyl, C1-C6-haloalkyl, —C1-C6-alkyl-C6-C10-aryl, C(O)C1-C6-alkyl, C(O)C1-C6-alkyl-C6-C10-aryl, C(O)OC1-C6-alkyl, C6-C10-aryl (optionally fused to C3-C14-cycloalkyl that is optionally substituted by one to four halo and C1-C6-alkyl), wherein
• each aryl is optionally substituted with one to three substituents selected from C1-C6-alkyl, halo, hydroxy, C1-C6-haloalkyl, and 3- to 14-membered heterocycloalkyl (wherein 1-4 ring members are independently selected from N, O, and S);
• each alkyl is optionally substituted with one to three substituents selected from halo, NRR′ (wherein R and R′ are independently selected from H, C1-C6-alkyl, C(O)C1-C6-alkyl, and C(O)C6-C10-aryl);
• R1L and R2L are independently selected from the group consisting of H, C1-C6-alkyl, C6-C10-aryl, —(C1-C6-alkyl)C6-C10-aryl, 5-10-membered heteroaryl (wherein 1-4 heteroaryl ring members are independently selected from the group consisting of O, S, and N), and C3-C14-cycloalkyl, wherein
• each aryl is optionally substituted with one to three substituents independently selected from the group consisting of C1-C6-alkyl, halo, C1-C6-haloalkyl, and C1-C6-alkoxy;
• each instance of R3L and R4L is independently selected from the group consisting of C1-C6-alkyl, halo, C1-C6-alkoxy, and C1-C6-haloalkyl;
• n is an integer selected from 1, 2, and 3;
• o is an integer selected from 0, 1, 2, and 3;
• and
• p is an integer selected from 0, 1, 2, and 3.