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. 2021 Apr 13;12(20):6964–6968. doi: 10.1039/d1sc00998b

Aza-Henry reaction optimization.

graphic file with name d1sc00998b-u1.jpg
Entrya PC x (mol%) Solvent λ (nm) Convb. (%)
1 ICG 10 CH3NO2c 810 16
2 IR-813 10 CH3NO2c 810 28
3 DTCCI 10 CH3NO2c 810 14
4 cy746 10 CH3NO2c 810 57
5 cy746 10 CH3NO2c 780 14
6 cy746 10 CH3NO2c 940 <5
7 cy746 10 DCM 810 48
8 cy746 10 DMF 810 n.r
9 cy746 10 MeOH 810 28
10 cy746 10 DMSO 810 91
11 cy746 5 DMSO 810 85
12 cy746 1 DMSO 810 67
13 cy746 DMSO 810 16
14d cy746 5 DMSO 810 n.r
15e cy746 5 DMSO 810 5
a

Run on 0.1 mmol scale.

b

Conversions are determined on the crude by 1H-NMR.

c

CH3NO2 is used as solvent.

d

Run in the dark.

e

Run under nitrogen atmosphere in the absence of air.