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. Author manuscript; available in PMC: 2011 Sep 1.
Published in final edited form as: J Am Chem Soc. 2010 Sep 1;132(34):12150–12154. doi: 10.1021/ja105834t

Table 2.

Ag2O-catalyzed fluorination of complex small molecules.

graphic file with name nihms227883t1.jpg
R′ = Me, Bu		 graphic file with name nihms227883t2.jpg graphic file with name nihms227883t3.jpg graphic file with name nihms227883t4.jpg
F-TEDA-PF6
graphic file with name nihms227883t5.jpg
flavanone 90%, 8 		graphic file with name nihms227883t6.jpg
Boc-Tyr-OMe 85%, 9 		graphic file with name nihms227883t7.jpg
maculosin 78%, 10 		graphic file with name nihms227883t8.jpg
quinine 75%, 11a 		graphic file with name nihms227883t9.jpg
DOPA 78%, 12
graphic file with name nihms227883t10.jpg
estrone 81%, 13 		graphic file with name nihms227883t11.jpg
Leu-enkephalin 83%, 14 		graphic file with name nihms227883t12.jpg
Boc-Tyr-Phe-OMe 92%, 15
graphic file with name nihms227883t13.jpg
estrol-17-β-D-lactosde heptabenzoate 80%, 16 		graphic file with name nihms227883t14.jpg
taxol 72%, 17 		graphic file with name nihms227883t15.jpg
rifamycin S 65%, 18b
a)

20 mol% of AgOTf, 2 equiv of NaOTf and 2 equiv of F-TEDA-PF6 were used at 90 °C.

b)

20 mol% of AgOTf, 2 equiv of NaOTf, and 5 equiv of MeOH was used. The names under the molecules in Table 2 refer to the parent molecules and not to fluorinated analogs shown.