Iodine(III)-mediated radiofluorination

A process for fluorodeiodination of an aromatic iodide compound comprising:

• (a) oxidizing an aromatic iodide compound (Ar-I), to form an iodonium compound;
• (b) reacting the iodonium compound with a compound of formula (A):
• to form an iodonium ylide;
• (c) reacting the iodonium ylide with a fluoride source to form an aromatic fluoride compound (Ar-F);
• wherein:
• Z1 is selected from the group consisting of NRZ1, O, and S;
• Z2 is selected from the group consisting of NRZ2, O, and S;
• RZ1 is selected from the group consisting of C3-10 cycloalkyl and C6-10 aryl, wherein said C3-10 cycloalkyl and C6-10 aryl forming RZ1 are each optionally substituted by 1, 2, 3, or 4 independently selected R20 groups;
• RZ2 is selected from the group consisting of C3-10 cycloalkyl and C6-10 aryl, wherein said C3-10 cycloalkyl and C6-10 aryl forming RZ2 are each optionally substituted by 1, 2, 3, or 4 independently selected R20 groups;
• RA is selected from the group consisting of H, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl;
• 2-methyl-1-butyl, n-pentyl, 3-pentyl, n-hexyl, 1,2,2-trimethylpropyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-10 aryl, 4-10 membered heterocycloalkyl, and 5-10 membered heteroaryl, wherein each of said C3-10 cycloalkyl, C6-10 aryl, 4-10 membered heterocycloalkyl, and 5-10 membered heteroaryl forming RA is optionally substituted by 1, 2, 3, or 4 independently selected R20 groups;
• RB is selected from the group consisting of H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-10 aryl, 4-10 membered heterocycloalkyl, and 5-10 membered heteroaryl, wherein each of said C3-10 cycloalkyl, C6-10 aryl, 4-10 membered heterocycloalkyl, and 5-10 membered heteroaryl forming RB is optionally substituted by 1, 2, 3, or 4 independently selected R20 groups;
• or RA and RB in combination, together with the carbon atom to which RA and RB are attached, form an oxo group;
• or RA and RB in combination, together with the carbon atom to which RA and RB are attached, form a 3, 4, 5, 6, or 7-membered carbocyclic or heterocyclic ring containing 3 to 7 carbon atoms and 0, 1, or 2 ring heteroatoms, each independently selected from N, O, and S, wherein the ring formed by the combination of RA and RB is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C1-6 hydroxyalkyl, and oxo;
• and
• and each R20 is independently selected from the group consisting of OH, SH, CN, NO2, halo, oxo, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 haloalkyl, C1-4 cyanoalkyl, C1-4 hydroxyalkyl, C1-4 alkoxy, —(C1-4 alkyl)-(C1-4 alkoxy), —(C1-4 alkoxy)-(C1-4 alkoxy), C1-4 haloalkoxy, C3-6 cycloalkyl, phenyl, 5-6 membered heteroaryl, 5-6 membered heterocycloalkyl, amino, C1-4 alkylamino, di(C1-4 alkyl)amino, carbamyl, C1-4 alkylcarbamyl, di(C1-4 alkyl)carbamyl, carbamoyl, C1-4 alkylcarbamoyl, di(C1-4 alkyl)carbamoyl, C1-4 alkylcarbonyl, C1-4 alkoxycarbonyl, C1-4 alkylcarbonylamino, C1-4 alkylsulfonylamino, aminosulfonyl, C1-4 alkylaminosulfonyl, di(C1-4 alkyl)aminosulfonyl, aminosulfonylamino, C1-4 alkylaminosulfonylamino, di(C1-4 alkyl)aminosulfonylamino, aminocarbonylamino, C1-4 alkylaminocarbonylamino, and di(C1-4 alkyl)aminocarbonylamino.