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. Author manuscript; available in PMC: 2019 Dec 21.
Published in final edited form as: J Org Chem. 2018 Dec 6;83(24):15493–15498. doi: 10.1021/acs.joc.8b02356

Table 2.

Reaction Optimizationa

graphic file with name nihms-1020500-t0006.jpg
entry solvent amine
(equiv)		 temp
(°C)		 time
(h)		 yield
(%)
1 6.5 mL of PBS 5 45 24 59
2 6.5 mL of PBSb 5 45 24 57
3 6.5 mL of PBSc 5 45 24 57
4 6.5 mL of PBS 5 30 24 66
5 6.5 mL of iPrOH 5 30 24 63
6 6.5 mL of THF 5 30 24 55
7 6.5 mL of PBS 2 30 24 62
8 6.5 mL of PBS 1 30 24 17
9 6.5 mL of PBS 0.5 30 24 n.d.d
10 6.5 mL of PBS 10 30 24 35
11 6.5 mL of PBS 2 30 18 56
12 10 mL of PBS 2 30 2 21e
13 10 mL of PBS 2 30 24 67
14 4 mL of PBS 2 30 24 62
15 2 mL of PBS 2 30 24 33
16 0.5 mL of PBS 2 30 24 19
17 neat 2 30 24 60
18 10 mL of PBS 2 0 8 48e
19 10 mL of PBS 2 30 8 55e
20f 10 mL of PBS 2 30 24 54e
21g 10 mL of PBS 2 30 24 50e
a

Reaction carried out in a ThermalSpa photoreactor on 0.5 mmol scale in solvent unless otherwise noted. Isolated yields are reported.

b

5% DMSO.

c

10% DMSO.

d

Complex mixture.

e

Starting material recoverable.

f

In a 20 mL Biotage microwave vial.

g

In a 25 mL Chemglass recovery flask.