Table 3 Heterogeneous visible light oxidative coupling of various amines into iminesa.

From: Elucidating heterogeneous photocatalytic superiority of microporous porphyrin organic cage

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Entry

Substrate

Product

t (min)

Conv. (%)b

TOFc

1

R=H

R=H

60

>99

33.0

2

R=F

R=F

50

>99

39.6

3

R=CH3

R=CH3

60

>99

33.0

4

R=OCH3

R=OCH3

70

>99

28.2

5

R=Cl

R=Cl

90

>99

22.0

6

50

>99

39.6

7

120

>99

16.5

8

140

>99

14.1

9d

R=H

R=H

180

>99

11.0

10e

R=H

R=H

120

>99

16.5

11f

R=H

R=H

300

>99

6.6

12g

R=H

R=H

60

25

8.3

13h

R=H

R=H

60

57

19.0

  1. aReaction conditions: 0.10 mmol substrate, 1.00 μmol PTC-1(2H) photocatalyst, 1.0 mL CD3CN, 1.0 atm O2, 25 W blue LED (420 nm < λem < 490 nm).
  2. bDetermined based on 1H NMR data.
  3. cTOF value was calculated by mmol of amine converted per mmol of porphyrin unit per hour.
  4. d3.00 μmol H2CBPP.
  5. e3.00 μmol PCN-222.
  6. f3.00 μmol PCN-224.
  7. g1.00 μmol PTC-1(2H) and 10.00 μmol DABCO.
  8. h1.00 μmol PTC-1(2H) and 10.00 μmol BQ.