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. 2023 Sep 26;88(19):14222–14226. doi: 10.1021/acs.joc.3c01534

Table 2. Cross-coupling Reactions with Borylated Atropisomers.

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No. Atropisomer/Aryl halide/Catalyst system/Conditions Yield [%] Stereoret. [% de]
1 4g, 4-Iodoacetophenone, Ni(COD)2, dppb, 2-MeTHF/H2O, i-Pr2EtN, 50 °C, 12 h 75 25
2 4g, 4-Bromoacetophenone, Ni[P(n-Bu)3]2(COD), dppb, 2-MeTHF/H2O, i-Pr2EtN, 50 °C, 12 h 81 74
3 4g, 4-Iodoacetophenone, Ni[P(n-Bu)3]2(COD), dppb, 2-MeTHF/H2O, i-Pr2EtN, 50 °C, 12 h 82 75
4 4k-SI, 4-Iodoacetophenone, Ni[P(n-Bu)3]2(COD), dppb, 2-MeTHF/H2O, i-Pr2EtN, 50 °C, 12 h 82 67
5 4g, 4-Iodoacetophenone, Ni[P(n-Bu)3]2(COD), 2-MeTHF/H2O, i-Pr2EtN, rt, 12 h 67 72
6 4g, 4-Iodoacetophenone, Ni(dppb)(COD), 2-MeTHF/H2O, i-Pr2EtN, rt, 12 h 85 71
7 4g, 4-Iodoacetophenone, Ni(dppb)(COD), 2-MeTHF/H2O, i-Pr2EtN, 50 °C, 0.5 h 10 70
8 4g, 4-Iodoacetophenone, Ni(dppb)(COD), 2-MeTHF/H2O, i-Pr2EtN, 50 °C, 2 h 33 69