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. 2023 Jan 13;14(7):1709–1714. doi: 10.1039/d2sc06055h

Optimisation of the reaction conditions. Reaction conditions: benzylamine (1a, 2.0 mmol), phenylboronic acid (2a, 0.5 mmol), isoamyl nitrite (2.5 mmol), sodium carbonate (0.5 mmol), chloroform (1.25 mL), 60 °C, 24 h.

graphic file with name d2sc06055h-u1.jpg
Entry Deviation from standard conditions Yielda [%]
1 No deviation 80 (70)b
2 No iAmONO 0
3 No base 72
4 Pinacol ester instead of phenylboronic acid 0
5 t BuONO instead of iAmONO 23
6 1 equiv. of boric acid (B(OH)3) 70
a

GC yield of the crude reaction mixture using n-dodecane as an internal standard.

b

Isolated yield.