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. 2023 Feb 15;26(3):105896. doi: 10.1016/j.isci.2022.105896

Table 1.

Optimization of the reaction conditions

Inline graphic
Entry Rh catalysta Base Solvent Temp. Yield ee
1 Rh2(S-DOSP)4 (1 mol %) DIPEA TFT 25°C 58% 59%
2 Rh2(S-PTTL)4 (1 mol %) DIPEA TFT 25°C 66% 87%
3 Rh2(S-PTAD)4 (1 mol %) DIPEA TFT 25°C 61% 91%
4 Rh2(S-BTPCP)4 (1 mol %) DIPEA TFT 25°C N.D.
5 Rh2(S-PTAD)4 (1 mol %) K2CO3 TFT 25°C N.R.
6 Rh2(S-PTAD)4 (1 mol %) CsCO3 TFT 25°C N.R.
7 Rh2(S-PTAD)4 (1 mol %) tBuOK TFT 25°C N.R.
8 Rh2(S-PTAD)4 (1 mol %) DIPEA Toluene 25°C 53% 82%
9 Rh2(S-PTAD)4 (1 mol %) DIPEA DCM 25°C 47% 20%
10 Rh2(S-PTAD)4 (1 mol %) DIPEA DMF 25°C Trace
11 Rh2(S-PTAD)4 (1 mol %) DIPEA TFT 40°C 73% 87%
12 Rh2(S-PTAD)4 (1 mol %) DIPEA TFT 0°C 21%
13 Rh2(S-PTAD)4 (0.5 mol %) DIPEA TFT 25°C 61% 92%
14 Rh2(S-PTAD)4 (0.25 mol %) DIPEA TFT 25°C 50% 74%
15b Rh2(S-PTAD)4 (0.5 mol %) DIPEA TFT 25°C 93% 95%
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N.D., Not detect.

a

Reaction conditions: N-Triftosylhydrazone 1 (0.2 mmol), 1,1-diphenylethylene 2 (0.1 mmol), [Rh] catalyst (1 mol %), DIPEA (N, N-diisopropylethylamine) (0.2 mmol), TFT (benzotrifluoride, 3.0 mL), 12 h, under N2.

b

α-Methyl-4-NO2-phenylethylene was used.