Table 2.

Homogeneous visible light oxidative coupling of various amines into imines^a.

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

^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.

^bDetermined by ¹H NMR analysis every 5 min.

^cTOF value was calculated by mmol of amine converted per mmol of porphyrin unit per hour.

^dNo irradiation.

^e3.00 μmol H₂CBPP.

^f3.00 μmol TPP.

^g0.10 μmol PTC-1(2H) and 5.00 μmol triethylenediamine (DABCO).

^h0.10 μmol PTC-1(2H) and 5.00 μmol benzoquinone (BQ).