Table 2 Homogeneous visible light oxidative coupling of various amines into iminesa.

From: Elucidating heterogeneous photocatalytic superiority of microporous porphyrin organic cage

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Entry

Catalyst

Atmosphere

t (min)

Conv. (%)b

TOFc

1

O2

15.0

Trace

2

PTC-1(2H)

O2

15.0

>99

1320

3

PTC-1(2H)

Air

20.0

>99

990

4

PTC-1(2H)

N2

15.0

Trace

5d

PTC-1(2H)

O2

15.0

Trace

6e

H2CBPP

O2

20.0

>99

990

7f

TPP

O2

25.0

>99

790

8g

PTC-1(2H)

O2

15.0

10

130

9h

PTC-1(2H)

O2

15.0

90

1200

  1. a0.10 mmol benzylamine, 0.10 μmol PTC-1(2H), 1.0 atm O2, 25 W blue LED (420 nm < λ < 490 nm), and 0.5 mL toluene-d8.
  2. bDetermined by 1H NMR analysis every 5 min.
  3. cTOF value was calculated by mmol of amine converted per mmol of porphyrin unit per hour.
  4. dNo irradiation.
  5. e3.00 μmol H2CBPP.
  6. f3.00 μmol TPP.
  7. g0.10 μmol PTC-1(2H) and 5.00 μmol triethylenediamine (DABCO).
  8. h0.10 μmol PTC-1(2H) and 5.00 μmol benzoquinone (BQ).