Table 1. Boron mediated disproportionation of formate anions into methoxyboranes a .
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Entry | R2B | BaseH+ | t c ] | T [°C] | Solvent | Yield b [%] |
1 | BBN | Et3NH+ | >48 h | 130 | d 8-THF | <5 |
2 | BBN | Et3NH+ | >48 h | 130 | C6D6 | <5 |
3 | BBN | Et3NH+ | 4 | 150 | CD3CN | 33 |
4 | BBN | Et3NH+ | 10.5 | 130 | CD3CN | 39 |
5 | BBN | iPr2EtNH+ | 4.5 | 130 | CD3CN | 50 |
6 | BCy2 | Et3NH+ | 2.5 | 130 | CD3CN | <5 |
7 | BCy2 | Et3NH+ | 7 | 120 | CD3CN | 38 |
aReaction conditions: 0.125 mmol 1– or 2–, 0.4 mL solvent.
bYields determined by 1H NMR using mesitylene (10 μL); mean value over at least 2 runs.
cTime required to obtain >95% conversion of formate.