Table 3.

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

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

^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 < λ_em < 490 nm).

^bDetermined based on ¹H NMR data.

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

^d3.00 μmol H₂CBPP.

^e3.00 μmol PCN-222.

^f3.00 μmol PCN-224.

^g1.00 μmol PTC-1(2H) and 10.00 μmol DABCO.

^h1.00 μmol PTC-1(2H) and 10.00 μmol BQ.