Table 1. Deviation of Reaction Conditions for the Trifluoromethylthiolation of 2aa.
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 |
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.
19F NMR yield using PhCF3 as the internal standard.
DCM was used as a solvent instead of MeCN.