Table 1.

Fluorinations of estrone (7), 13α-estrone (12), 17-deoxyestrone (13) or 17-deoxy-13α-estrone (14) with Selectfluor (2).

Entry	Substrate	Solvent	Temperature	Reaction Time	Product	Yield (%)
1	7	acetonitrile	rt	24 h	9	95
2	7	acetonitrile	80 °C	1 h	9	97
3 a	7	acetonitrile	rt	24 h	9	3
4	7	methanol	rt	24 h	9 + (15 + 16) b	76 + (16)
5	7	methanol	reflux	1 h	9 + (15 + 16)	78 + (15)
6 a	7	methanol	rt	24 h	9	2
7	12	acetonitrile	rt	24 h	17	97
8	12	acetonitrile	80 °C	1 h	17	98
9 a	12	acetonitrile	rt	24 h	17	4
10	12	methanol	rt	24 h	17 + (18 + 19) c	71 + (12)
11	12	methanol	reflux	1 h	17 + (18 + 19)	73 + (13)
12 a	12	methanol	rt	24 h	17	94
13	13	acetonitrile	rt	24 h	20	94
14	14	acetonitrile	rt	24 h	21	92

^a 2 equiv. of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO); ^b Ratio: 15:16 = 1:0.9; ^c Ratio: 18:19 = 1:1.5.