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. Author manuscript; available in PMC: 2011 May 21.
Published in final edited form as: J Org Chem. 2010 May 21;75(10):3332–3338. doi: 10.1021/jo100361d

Table 2.

Radiochemical Yields of [18F]Fluoroarenes from the Radiofluorination of o-Substituted Diaryliodonium Salts.

Entrya Diaryliodonium salt
(ArI+Ar’X)		 Temp.
(°C)		 Time
(s)		 RCY of [18F]fluoroarene
(%)		 Selectivity
for main
product		 GTs1-GTs2
(kcal/mol)
Ar Ar’ Total Ar18F Ar’18F
1 Ph Ph 110 377 85 85 - - -
2 2-MeC6H4 2-MeC6H4 140 ” 83 83 - - -
3 2-MeC6H4 Ph 110 ” 82 57 25 2.28 0.63
4 Ph 2-MeOC6H4 140 ” 66 60   6.5 9.22 1.8
5 2-MeC6H4 2-MeOC6H4 ” ” 79 75   4 18.8 2.4
6 2-MeOC6H4 2-MeOC6H4 ” ” 51 51 - - -
7 2-BrC6H4 2-MeC6H4 170 471 86 48 38 1.26 0.20
8 2-MeC6H4 2-EtC6H4 ” ” 95 52 43 1.21 0.17
9 2-MeC6H4 2-iPrC6H4 ” ” 88 48 40 1.20 0.16
10 2,6-di-MeC6H3 2-MeC6H4 ” ” 74 62 11 5.56 1.5
11 2,4,6-tri-MeC6H2 2-MeC6H4 130 ” 92 59 33 1.78 0.46
12 2,4,6-tri-MeC6H2 Ph 150 ” 82 63 19 3.24 0.99
13 2,6-di-MeC6H3 2,4,6-tri-MeC6H2 190 ” 82 61 21 3.00 1.0
14 2-BrC6H4 Ph ” ” 93 68 25 2.72 0.92
a

Entries 1–6 were performed with CA [18F]fluoride ion and chloride salts in DMF-0.25% water. Entries 7–11 and 14 were performed with NCA [18F]fluoride ion and chlorides in DMF. Entries 12 and 13 were performed with NCA [18F]fluoride ion and tosylates in DMF.