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. 2019 May 6;10(23):5990–5995. doi: 10.1039/c9sc00829b

Table 3. 1,1-Trifluoromethylthiolation–phenylation of diazo compounds 2 with SCF3-source 1 and Bu4N(BPh)4 (3a) a .

Inline graphic
Entry Diazocarbonyl compound 2 Carbonyl compound 5 Yield b of 5 (%)
1 graphic file with name c9sc00829b-u4.jpg graphic file with name c9sc00829b-u5.jpg 81
2 graphic file with name c9sc00829b-u6.jpg graphic file with name c9sc00829b-u7.jpg 80
3 graphic file with name c9sc00829b-u8.jpg graphic file with name c9sc00829b-u9.jpg 73
4 graphic file with name c9sc00829b-u10.jpg graphic file with name c9sc00829b-u11.jpg 84
5 graphic file with name c9sc00829b-u12.jpg graphic file with name c9sc00829b-u13.jpg 60
6 graphic file with name c9sc00829b-u14.jpg graphic file with name c9sc00829b-u15.jpg 68 c
7 graphic file with name c9sc00829b-u16.jpg graphic file with name c9sc00829b-u17.jpg 84
8 graphic file with name c9sc00829b-u18.jpg graphic file with name c9sc00829b-u19.jpg 30 c
9 graphic file with name c9sc00829b-u20.jpg graphic file with name c9sc00829b-u21.jpg 83
10 graphic file with name c9sc00829b-u22.jpg graphic file with name c9sc00829b-u23.jpg 48
11 graphic file with name c9sc00829b-u24.jpg graphic file with name c9sc00829b-u25.jpg 78(74) d
12 graphic file with name c9sc00829b-u26.jpg graphic file with name c9sc00829b-u27.jpg 80
13 graphic file with name c9sc00829b-u28.jpg graphic file with name c9sc00829b-u29.jpg 0
14 graphic file with name c9sc00829b-u30.jpg graphic file with name c9sc00829b-u31.jpg 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.