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. 2021 Sep 13;11(48):30398–30406. doi: 10.1039/d1ra04736a

Summary of the screening of conditions done in a flow chemistry reactora.

graphic file with name d1ra04736a-u2.jpg
No. Conc. (M) Press. (bar) T (°C) Equiv. CO Equiv. Cat. R. t. (min) Ratio 5 : 2b Yieldc5 (%)
1d 0.25 15 220 0.3 60 60 : 40 56
2 0.25 20 220 0 1 8 60 : 40 55
3 0.25 20 220 5 0.3 8.5 48 : 52 45
4e 0.25 20 220 3 0.3 8.5 53 : 47 54
5 0.1 20 220 3 0.3 7 48 : 52 n.i.f
6 0.5 20 220 3 0.3 8 48 : 52 48
7 0.25 20 220 3 0.15 7 31 : 69 n.i.f
8 0.25 28 220 3 0.3 9 45 : 55 n.i.f
9 0.25 10 220 3 0.3 6 31 : 69 n.i.f
10 0.25 20 240 3 0.3 7 43 : 57 n.i.f
11 0.25 20 200 3 0.3 7 40 : 60 n.i.f
12g 0.25 20 220 3 0.3 7.5 57 : 43 56
13h 0.25 20 220 3 0.3 8.5i 60 : 40 55
a

All reactions were performed with 1.0 equiv. of the amine and 2.0 equiv. of thiol (method C).

b

Ratio estimated based on the integrals of well resolved 1H NMR signals of the crude mixture.

c

In pure product.

d

Batch reaction.

e

Method-C.

f

Isolation was not done.

g

Including 1.0 equiv. of AcOH (method D).

h

Long run with 1 g of amine.

i

52 min of total operation time.