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. 2020 Jul 1;142(33):14045–14051. doi: 10.1021/jacs.0c05131

Table 1. Optimization of the Reaction Conditionsa.

graphic file with name ja0c05131_0006.jpg

entry R1 R2 cat. solvent yieldb e.r.c
1 Bn Bn A CH2Cl2 traces
2 Me Bn A CH2Cl2 traces
3 Me Bzh A CH2Cl2 14% 55:45
4 Me Bzh B CH2Cl2 20% 55:45
5 Me Bzh C CH2Cl2 20% 75:25
6 Me Bzh D CH2Cl2 45% 74:26
7 Me Bzh D CHCl3 56% 67:33
8 Me Bzh D 1,2-DFB 47% 79:21
9 Me Bzh D 1,2-DCE 51% 81:19
10 Et Bzh D 1,2-DCE 40% 96:4
11d,e Et Bzh D 1,2-DCE 93% 96:4
12 Bn Bzh D 1,2-DCE >95% 96:4
13d,f Bn Bzh D 1,2-DCE 98% 96:4
a

Reaction conditions: 0.05 mmol of 1, 0.25 M, 10 mol% cat., stirring at 900 rpm, 24 h.

b

Determined by 19F NMR spectroscopy with 4-fluoroanisole as an internal standard.

c

Enantiomeric ratios were determined by HPLC using a chiral stationary phase.

d

Yield of isolated product.

e

72 h, 10 mol% cat.

f

48 h, 5 mol% cat.