Table 3. 1,1-Trifluoromethylthiolation–phenylation of diazo compounds 2 with SCF3-source 1 and Bu4N(BPh)4 (3a) a .
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Entry | Diazocarbonyl compound 2 | Carbonyl compound 5 | Yield b of 5 (%) |
1 |
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81 |
2 |
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80 |
3 |
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73 |
4 |
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84 |
5 |
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60 |
6 |
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68 c |
7 |
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84 |
8 |
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30 c |
9 |
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83 |
10 |
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48 |
11 |
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78(74) d |
12 |
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80 |
13 |
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0 |
14 |
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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.