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. 2022 Dec 27;8(1):1060–1066. doi: 10.1021/acsomega.2c06417

Table 1. Reaction Optimization Conditionsa.

graphic file with name ao2c06417_0007.jpg

entry deviation in conditions yield (%)
1 standard conditions 79 (63%)
2 2 equiv Zn(0) 21
3 2 equiv Mn(0) 24
4 2 equiv TDAE 43
5 no reductant <1
6 diethylzinc bromide <1
7 phenethylzinc bromide 58
8 no additives 49
9 dioxanylzinc bromide 56
10 cyclopropylzinc bromide 59
11 tert-butylzinc bromide 46
12 1-ethylpropylzinc bromide 70
13 DMF instead of NMP 66
14 DMSO instead of NMP 70
15 toluene instead of NMP 25
16 THF instead of NMP 29
17 MeCN instead of NMP 0
a

0.1 mmol scale reactions in 0.5 mL of solvent.1H NMR yields using pyrene as an internal standard. The value in parentheses is the isolated yield [diastereomeric ratio (dr) = 1:1] from 0.5 mmol. The dr was determined by 1H NMR of the crude reaction mixture.