Selective hydrodeoxygenation of aromatic compounds

A method comprising:

• selectively deoxygenating at least one oxygenated aromatic compound in the presence of a hydrogen gas and a catalyst system to form a reaction product, wherein the catalyst system comprises a complex of formula (I):
• wherein
• R1 is hydrogen, OH, halogen, amine, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, C6-C14 aryloxy, C3-C10 cycloalkyl, or C3-C10 cycloalkenyl, wherein R1 is optionally substituted with C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, phosphonyl;
• each R2 is, independent of the other, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C6-C14 aryl, or C1-C13 heteroaryl, wherein R2 is optionally substituted with C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, or thiol;
• each R3 and R4 are, independent of the other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C6-C14 aryl, or C1-C13 heteroaryl, wherein R3 and R4 are optionally substituted with C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, or thiol, or R3 and R4 combine together with the atoms to which they are attached to form a cycloalkene ring, heteroaromatic ring, or aromatic ring;
• each R16 and R17 are, independent of the other, hydrogen, OH, halogen, amine, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, C6-C14 aryloxy, C3-C10 cycloalkyl, or C3-C10 cycloalkenyl, wherein each R16 and R15, independent of the other, is optionally substituted with C1-C10 alkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C14 aryl, C1-C13 heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, cyano, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiol, or phosphonyl;
• M is Ru or Ir;
• each L is independently selected from C1, Br, CH3CN, DMF, H2O, bipyridine, phenylpyridine, CO2, and a CNC-pincer ligand;
• and
• n is 1, 2, or 3;
• wherein the oxygenated aromatic compound has the formula:
• wherein
• R6 is independently selected from hydrogen, substituted or unsubstituted C1-C6-alkyl, substituted or unsubstituted C3-C10 cycloalkyl and heteroalkyl, C2-C10 alkenyl, and Ar′;
• R7 is independently selected from hydrogen, substituted or unsubstituted C1-C6-alkyl, substituted or unsubstituted C3-C10 cycloalkyl and heteroalkyl, C2-C10 alkenyl, and Ar′;
• R8 is independently selected from hydrogen, substituted or unsubstituted C1-C6-alkyl, substituted or unsubstituted C3-C10 cycloalkyl and heteroalkyl, C2-C10 alkenyl, and Ar′;
• R9 is independently selected from hydrogen, substituted or unsubstituted C1-C6-alkyl, substituted or unsubstituted C3-C10 cycloalkyl and heteroalkyl, C2-C10 alkenyl, and Ar′;
• R10 is independently selected from hydrogen, substituted or unsubstituted C1-C6-alkyl;
• substituted or unsubstituted C3-C10 cycloalkyl and heteroalkyl, C2-C10 alkenyl, and Ar′;
• wherein R11 is a bond, substituted or unsubstituted C1-C6 alkylene, C2-C10 alkenylene, or Ar″;
• R18 is independently selected from substituted or unsubstituted C1-C6-alkylene, C2-C10 alkenylene, and Ar″;
• R19 is independently selected from substituted or unsubstituted C1-C6-alkyl, substituted or unsubstituted C3-C10 cycloalkyl and heteroalkyl, C2-C10 alkenyl, and Ar′;
• Ar′ is a C6-C14 aryl or heteroaryl group optionally substituted with 1, 2, or 3 substituents;
• Ar″ is a C6-C14 arylene or heteroarylene group optionally substituted with 1, 2, or 3 substituents;
• wherein Ar′ and Ar″ are the same or different, and
• wherein the reaction product has the formula: