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. 2020 May 22;85(13):8311–8319. doi: 10.1021/acs.joc.0c01030

Table 1. Deviation of Reaction Conditions for the Trifluoromethylthiolation of 2aa.

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entry additive yieldb of 4a (%) yieldb of 5a (%) recoveryb of 2a (%)
1 1.0 equiv of KF 78 3
2 1.0 equiv of CsF 61 6
3 1.0 equiv of TBAF·3H2O 15 45
4 1.0 equiv of TBAT 41 3
5 10 mol % of DABCO 70
6 10 mol % of FeCl2 8 78
7c 1.0 equiv of KF 76
8 trace 75
a

General procedure: 2a (0.1 mmol), 3 (0.1 mmol), and additive were stirred in MeCN (0.5 mL) at room temperature for 3 h.

b

19F NMR yield using PhCF3 as the internal standard.

c

DCM was used as a solvent instead of MeCN.