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. Author manuscript; available in PMC: 2012 Oct 21.
Published in final edited form as: Org Lett. 2011 Sep 20;13(20):5464–5467. doi: 10.1021/ol202174a

Table 2.

Substrate Scope of Silver-Mediated Trifluoromethylation[a][b]

graphic file with name nihms326509t2.jpg

entry substrate major product yield (%) isomer ratio
1[c] graphic file with name nihms326509t3.jpg graphic file with name nihms326509t4.jpg 87 ---
2 graphic file with name nihms326509t5.jpg graphic file with name nihms326509t6.jpg 81 a : b : c
2.7 : 1.4 : 1
3 graphic file with name nihms326509t7.jpg graphic file with name nihms326509t8.jpg 76 ---
4 graphic file with name nihms326509t9.jpg graphic file with name nihms326509t10.jpg 76 a : b : c
5.2 : 3.5 : 1
5 graphic file with name nihms326509t11.jpg graphic file with name nihms326509t12.jpg 65 a : b
1.4 : 1
6 graphic file with name nihms326509t13.jpg graphic file with name nihms326509t14.jpg 78 ---
7 graphic file with name nihms326509t15.jpg graphic file with name nihms326509t16.jpg 87 a : b : c
2.7 : 1.2 : 1
8[c] graphic file with name nihms326509t17.jpg graphic file with name nihms326509t18.jpg 88 ---
9 graphic file with name nihms326509t19.jpg graphic file with name nihms326509t20.jpg 85 a : b : c
13 : 7.3 : 1
10 graphic file with name nihms326509t21.jpg graphic file with name nihms326509t22.jpg 70 a : b
4 : 1
11[c] graphic file with name nihms326509t23.jpg graphic file with name nihms326509t24.jpg 46 a : b : c
1.7 : 1.2 : 1
12[c] graphic file with name nihms326509t25.jpg graphic file with name nihms326509t26.jpg 44 a : b
>20 : 1
13 graphic file with name nihms326509t27.jpg graphic file with name nihms326509t28.jpg 72 a : b
8 : 1
14[d] graphic file with name nihms326509t29.jpg graphic file with name nihms326509t30.jpg 70 a : b
4.8 : 1
15[d] graphic file with name nihms326509t31.jpg graphic file with name nihms326509t32.jpg 42 ---
[a]

General conditions: substrate (10 equiv), TMSCF3 (1 equiv) in DCE at 85 °C for 24 h.

[b]

Yield and selectivity determined by 19F NMR analysis of the crude reaction mixtures.

[c]

20 equiv substrate used.

[d]

5 equiv substrate used.