Photoredox-catalyzed direct C—H functionalization of arenes

A method of making a compound having a structure represented by a formula:

• wherein E is an electron donating group;
• wherein each of Q1 and Q3 is independently selected from N and CR1;
• wherein each of Q2 and Q4 is independently selected from N and CR2;
• wherein each occurrence of R1 and R2 is independently selected from hydrogen, halogen, C1-C8 alkyl, C1-C8 alkoxy, and C(═O)NR3aR3b;
• or
• wherein R1 and R2 are optionally covalently bonded and, together with the intermediate atoms, comprise a 5- to 6-membered cycle or heterocycle having 0, 1, or 2 heteroatoms and substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C8 alkyl, C1-C8 alkoxy, and C(═O)NR3aR3b;
• wherein each of R3a and R3b is independently selected from hydrogen and C1-C4 alkyl;
• wherein Z is selected from —NH2, C1-C8 alkylamino, (C1-C8)(C1-C8) dialkylamino, arylamino, diarylamino, and C1-C8 alkarylamino;
• wherein R4 is selected from hydrogen and C1-C8 alkyl;
• wherein R5 is selected from C1-C8 alkyl;
• wherein Ar1 is a 3- to 6-membered heterocycle substituted with 0, 1, 2, or 3 groups independently selected from halogen and C1-C8 alkyl,
• the method comprising the steps of:
• (a) reacting a compound having a structure represented by a formula:
• with a nucleophile selected from ammonia and an amine, in the presence of a catalytically effective amount of an acridinium photocatalyst;
• and
• (b) reacting with an oxidant,
• thereby forming the compound.