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. Author manuscript; available in PMC: 2022 Dec 22.
Published in final edited form as: J Am Chem Soc. 2021 Dec 13;143(50):21223–21228. doi: 10.1021/jacs.1c10541

Table 1.

Reaction optimization

graphic file with name nihms-1818929-t0004.jpg
Entry time (h) 3 (eq) Lamp (nm) Solvent 2ah % 4ah % 5h %
1a,f 3 7.5 390 EtOAc 6 15 59
2 a,f 3 7.5 390 CH3CN 5 16 57
3 b,f 3 7.5 390 EtOAc 7 29 40
4 a,f 3 7.5 390 CH3CN 6 26 37
5 g 3 7.5 390 neat 18 38 23
6 f 3 15 390 neat 6 47 28
7 g 3 7.5 370 neat 44 26 19
8 g 3 7.5 427 neat 40 30 17
9 g 3 7.5 440 neat 58 21 11
10 g 3 7.5 456 neat 76 12 7
11 g 3 7.5 525 neat 98 0 0
12 e,g 3 7.5 -- neat 99 0 0
13 c,g 3 7.5 390 neat 20 33 20
14 d,g 3 7.5 390 neat 22 37 22
15 c,g 16 7.5 390 neat -- 36 8
16 d,g 16 7.5 390 neat -- 36 9
17 g 16 7.5 390 neat -- 48 9
a

0.65 mL.

b

0.172 mL.

c

no Aldrithiol.

d

no freeze-pump-thaw.

e

60 °C and shielded from light.

f

0.2 mmol imine.

g

0.4 mmol imine.

h

yield based on Q1HNMR analysis with 1,3,5-trimethoxybenzene internal standard