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. 2017 Jan 18;23(9):2217–2224. doi: 10.1002/chem.201605466

Table 1.

Initial optimization of BPh3‐catalysed reductive amination. Inline graphic

Entry Solvent Silane Equiv. Silane Temp. [°C] Yield [%][a]
1 o‐DCB PhMe2SiH 1.2 100 <5
2 MeCN PhMe2SiH 1.2 100 33
3 o‐DCB PhMe2SiH 3.5 100 <5
4 MeCN PhMe2SiH 3.5 100 87 (80)[b]
5c MeCN PhMe2SiH 3.5 100 35
6 MeCN PhMe2SiH 3.5 60 6
7 MeCN Ph2SiH2 3.5 100 86
8 MeCN Ph2MeSiH 3.5 100 8
9 MeCN PhMeSiH2 3.5 100 55
10 MeCN PhSiH3 3.5 100 56

Reactions performed in sealed tubes. [a] Yield by 1H NMR spectroscopy versus mesitylene as internal standard. [b] Isolated yield. [c] Reaction at 5 mol % catalyst loading.