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. 2021 Aug 20;12(38):12695–12703. doi: 10.1039/d1sc03268b

Selected optimisation results of the racemic Pd-AAA reactions of cyclic imine 2a with allyl carbonate 1a using triphenylphosphinea.

graphic file with name d1sc03268b-u1.jpg
Entry Solvent Yieldb (%)
3aa 4aa
1 MeCN 49c 30c
2d,e MeCN 77
3 CH 2 Cl 2 70
4 THF 89
5 PhMe NR
6 MeOH 16 17
7 DMF 41 22
8 DMSO 61 12
a

Reaction conditions: 1a (0.2 mmol, 1.0 equiv.), 2a (0.22 mmol, 1.1 equiv.), [Pd(π-C3H5)Cl]2 (5 mol%), PPh3 (15 mol%), solvent (0.07 M w.r.t. 1a), rt, 21 h.

b

Yield determined by 1H NMR integration against an internal standard (1,2,3-trimethoxybenzene).

c

Isolated yield.

d

4aa was employed as the SM.

e

Reaction time: 17 h.