Process for deoxyfluorination of phenols

A method of replacing a hydroxyl group on an aryl or heteroaryl compound bearing the hydroxyl group with a fluorine atom, the method comprising contacting a compound of Formula (I):

• with a Cp-Ru-(aryl or heteroaryl)-complex in the presence of a fluorine source under conditions sufficient to fluorinate the aryl or heteroaryl compound bearing the hydroxyl group compound, thereby providing a fluorinated (aryl or heteroaryl) compound, wherein, in Formula (I):
• R1 and R2 are independently selected from the group consisting of C1-30 aliphatic, aromatic, heteroaliphatic or heteroaromatic hydrocarbons, each of which is optionally substituted with at least one substituent selected from C1-20 straight chain, branched or cyclic alkyl, alkenyl, alkynyl, aryl, heteroaryl, each being optionally further substituted by one or more heteroatoms, or heteroatoms,
• R3 and R4 are independently selected from the group consisting of C1-30 aliphatic, aromatic, heteroaliphatic or heteroaromatic hydrocarbons, each of which is optionally substituted with at least one substituent selected from C1-20 straight chain, branched or cyclic alkyl, alkenyl, alkynyl, aryl, heteroaryl, each being optionally further substituted by one or more heteroatoms, or heteroatoms, or
• R3 and R4 together with N—C═N to which they are bonded form a C4-20 ring which may be saturated or unsaturated aliphatic or aromatic, which C4-20 ring is optionally substituted with at least one substituent selected from C1-20 straight chain, branched or cyclic alkyl, alkenyl, alkenyl, aryl, heteroaryl, the C4-20 ring being optionally further substituted by one or more heteroatoms, or heteroatoms, and the C4-20 ring optionally fused to a C5-20 hydrocarbon ring which may be unsaturated or saturated aliphatic or aromatic including heteroatoms, which C5-20 hydrocarbon ring is optionally substituted by at least one substituent selected from C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, nitro, cyano, halo, C1-6 haloalkyl, C1-6 alkoxy, optionally substituted C6-10 aryl, optionally substituted C6-10 aralkyl, optionally substituted 5-10 membered heteroaryl, optionally substituted 4-10 membered heterocyclyl, optionally substituted 3-10 membered carbocyclyl, optionally substituted 4-10 membered heterocyclylalkyl, and acyl, each substituent for the C5-20 hydrocarbon ring being optionally further substituted by one or more heteroatoms;
• X being an anion;
• and
• L being a leaving group,
• wherein the Cp-Ru-(aryl or heteroaryl)-complex is a Ru complex with a C5 to C30 aromatic or heteroaromatic mono- to polycyclic ring system having at least one aromatic or heteroaromatic ring with one hydroxyl group on said ring, said ring system optionally being further substituted with straight chain, branched or cyclic alkyl, alkenyl or alkynyl having 1 to 20 carbon atoms, or heteroatoms being selected from halogen, N, O or S, each of said alkyl, alkenyl, alkynyl, or heteroatoms being optionally further substituted or each of said alkyl, alkenyl, alkynyl, or heteroatoms being optionally part of an aliphatic or aromatic ring system, and at least one further ligand optionally being further substituted by one or more heteroatoms or by C1-6 alkyl, optionally being further substituted with halogen.