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. 2021 Jul 21;12(35):11831–11838. doi: 10.1039/d1sc02636d

Optimization of reaction conditions for Ir-catalyzed reaction of racemic allenyl carbonate 1a with benzylamine 2aa.

graphic file with name d1sc02636d-u2.jpg
Entry n T/°C Yield of 3aab (%) Yield of 4aab (%) Recovery of 1ab (%)
1 1.5 r.t. 26 25
2c 1.5 r.t. 24 27
3 2 r.t. 35 28
4 4 r.t. 41 6 38
5d 4 r.t. 45 7 45
6d 4 40 64 8 11
7d 4 50 70 8
8d 4 60 65 9
a

The reaction was conducted using 1a (0.2 mmol) in 0.4 mL of THF.

b

Determined by 1H NMR analysis of the crude reaction mixture using 1,3,5-trimethylbenzene as an internal standard.

c

7 mol% Ir pre-catalyst A was used.

d

The reaction was conducted using 1a (0.2 mmol) in 1.0 mL of THF.