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. 2020 Jul 23;11(37):10061–10070. doi: 10.1039/d0sc01939a

Optimization of the reaction conditions and evaluation of key parameters for the reaction selectivitya.

Entry Base 3aa, % 4aa, % 5aa, % 6aa, %
1 Py 0 0 90 10
2 NaHCO3 29 2 62 7
3 KOAc 44 4 47 5
4 K2CO3 70 13 7 10
5 KF 81 7 10 2
6b tBuOK 33 5 0 62
7 DBU 85 7 3 0
8c DBU 10 77 0 0
9c,d,e DBU 0 0 7 93
10f DBU 5 0 37 58
11e DBU 0 0 0 22
12e,c DBU 0 0 0 23
13g DBU 0 92 0 0
14h DBU 1 0 1 12
a

Unless otherwise noted, the reactions were carried out using 1a (0.15 mmol), 2a (0.3 mmol), DMF (3 ml), base (0.33 mmol), Eosin Y (3 mol%), 40 °C, green LEDs (1.25 W), 24 h, and argon.

b

Reaction mixture was deeply colored.

c

Under air.

d

t = 80 °C, reaction time 72 h.

e

Reaction without Eosin Y and green light.

f

0.125 ml of DMF.

g

Addition of TEMPO.

h

Addition of γ-terpinene. Several reaction mixtures' NMR spectra are shown in the ESI (Fig. S1–S4).