Table 3. 1,1-Trifluoromethylthiolation–phenylation of diazo compounds 2 with SCF3-source 1 and Bu4N(BPh)4 (3a) a .
| |||
Entry | Diazocarbonyl compound 2 | Carbonyl compound 5 | Yield b of 5 (%) |
1 | 81 | ||
2 | 80 | ||
3 | 73 | ||
4 | 84 | ||
5 | 60 | ||
6 | 68 c | ||
7 | 84 | ||
8 | 30 c | ||
9 | 83 | ||
10 | 48 | ||
11 | 78(74) d | ||
12 | 80 | ||
13 | 0 | ||
14 | 55 c , e , f |
aUnless otherwise stated: to 1 (0.1 mmol), Bu4N(BPh4) (3c) (0.15 mmol), Zn(NTf2)2 (4) (0.05 mmol) and 3Å ms (80 mg) was added a solution of 2 (0.15 mmol) in CH2Cl2 (1.0 ml) at –10 °C, stirred for 2 h before warmed up to RT overnight.
bUnless otherwise stated isolated yield.
cRT overnight.
d1.0 mmol scale.
eInstead of 1, NFSI was used.
fYield of 6 (determined by 1H-NMR analysis) contains side product 1-(4-nitrophenyl)-2-phenylethan-1-one.