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. Author manuscript; available in PMC: 2020 Sep 18.
Published in final edited form as: J Org Chem. 2017 Jan 31;82(4):2231–2236. doi: 10.1021/acs.joc.6b02863

Table 3.

Oxidation of Fluoroalcohols 10–18 to 2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones 19–27.

graphic file with name nihms-1627056-t0025.jpg
entry substrate product yielda
1 10 graphic file with name nihms-1627056-t0026.jpg 80%
2 11 graphic file with name nihms-1627056-t0027.jpg 78% (99%)b
3 12 graphic file with name nihms-1627056-t0028.jpg 79% (90%)b
4 13 graphic file with name nihms-1627056-t0029.jpg 88% (100%)b
5 14 graphic file with name nihms-1627056-t0030.jpg 84% (95%)b
6 15 graphic file with name nihms-1627056-t0031.jpg 80% (97%)b
7 16 graphic file with name nihms-1627056-t0032.jpg 79% (88%)b
8 17 graphic file with name nihms-1627056-t0033.jpg 41% (54%)b
9 18 graphic file with name nihms-1627056-t0034.jpg 95%c
a

Isolated yields

b

Yields determined by 19F NMR

c

Reference 18.