Table 1 Reaction condition optimization
From: Pd-catalyzed deuteration of aryl halides with deuterium oxide
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entry | Pd/L | diboron | additive | T (°C) | yield (%) | D (%) |
1 | Pd(tBu3P)2 | B2cat2 | tBuOK | 70 | 43 | 42 |
2 | Pd(tBu3P)2 | B2cat2 | DABCO | 70 | 43 | 65 |
3 | Pd(tBu3P)2 | B2cat2 | AgOTf | 70 | <5 | -- |
4 | Pd(tBu3P)2 | B2cat2 | Zn(BF4)2·H2O | 70 | 47 | 17 |
5 | Pd(tBu3P)2 | B2cat2 | Zn(OTf)2 | 70 | 58 | 50 |
6 | Pd(tBu3P)2 | B2cat2 | Zn(OAc)2 | 70 | 56 | 71 |
7 | Pd(tBu3P)2 | B2cat2 | ZnO | 70 | 89 | 89 |
8 | Pd(tBu3P)2 | B2eg2 | ZnO | 70 | 55 | 82 |
9 | Pd(tBu3P)2 | B2pin2 | ZnO | 70 | <5 | -- |
10 | Pd(tBu3P)2 | B2hex2 | ZnO | 70 | <5 | -- |
11 | Pd(PPh3)4 | B2cat2 | ZnO | 70 | 36 | 83 |
12 | Pd(Amphos)2 | B2cat2 | ZnO | 70 | 81 | 89 |
13 | AdBrettPhos Pd G3 | B2cat2 | ZnO | 70 | 44 | 87 |
14 | SPhos Pd G3 | B2cat2 | ZnO | 70 | 92 | 93 |
15 | SPhos Pd G3 | B2cat2 | ZnO | 25 | 78 | 87 |
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