Table 1. Catalytic dihydroboration of organonitriles with HBpin and 10 mol% V.
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Entry | R | Time (h) | NMR yield a (%) | Isolated yield a (%) |
1 | Et | 0.5 | >99 | 70 |
2 | i-Pr | 1 | 93 | 96 |
3 | t-Bu | 5.5 | 97 | 54 |
4 | Cy | 1 | 94 | 75 |
5 | C6H5 | 12 | 92 | 56 |
6 | o-(Me)C6H4 | 15 | 86 | 73 |
7 | m-(Me)C6H4 | 15 | 87 | 81 |
8 | m-(F)C6H4 | 14 | 88 | 57 |
9 | m-(MeO)C6H4 | 15 | 90 | 60 |
10 | p-(Me)C6H4 | 13 | 91 | 72 |
11 | p-(F)C6H4 | 12 | 94 | 61 |
12 | p-(Cl)C6H4 | 12 | 93 | 59 |
13 | p-(CF3)C6H4 | 12.5 | 89 | 76 |
14 | p-(MeO)C6H4 | 13.5 | 88 | 58 |
15 | Ph2CH | 30 | 75 | 43 |
aAll NMR reactions were carried out in C6D6 whilst scale-up reactions were carried out in toluene then isolated from hexanes.