Mixed hetero-/homogeneous TiO2/N-hydroxyimide photocatalysis in visible-light-induced controllable benzylic oxidation by molecular oxygen

doi:10.1016/S1872-2067(21)63831-7

Abstract

Abstract:

Homogeneous and heterogeneous types of catalysis are frequently considered as separate disciplines or even opposed to each other. In the present work, a new type of mixed hetero-/homogeneous catalysis was demonstrated for the case of selective alkylarene oxidation by molecular oxygen. The proposed catalytic system consists of two widely available components: N-hydroxyphthalimide (NHPI, a homogeneous organocatalyst for free-radical chain reactions) and nanosized TiO₂ (heterogeneous UV-active photoredox catalyst). The interaction of NHPI with TiO₂ allows for a shift from UV to visible light photoredox activity and generation of phthalimide-N-oxyl (PINO) radicals that diffuse into the solution where NHPI/PINO-catalyzed free-radical chain reaction can proceed without the additional light input providing a fundamental increase in energy efficiency. The NHPI/TiO₂ ratio controls the selectivity of oxidation affording preferential formation of hydroperoxide or ketone from alkylarene.

Key words: TiO₂, Photoredox catalysis, N-hydroxyphthalimide, N-oxyl radicals, Aerobic oxidation

Igor B. Krylov, Elena R. Lopat’eva, Irina R. Subbotina, Gennady I. Nikishin, Bing Yu, Alexander O. Terent’ev. Mixed hetero-/homogeneous TiO₂/N-hydroxyimide photocatalysis in visible-light-induced controllable benzylic oxidation by molecular oxygen[J]. Chinese Journal of Catalysis, 2021, 42(10): 1700-1711.

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Consumed power (W)	Irradiance * (W/m²)	Relative irradiated power
10	1165	1
5	700	0.6
2.5	407	0.35
1	203	0.17

Consumed power (W)	Irradiance * (W/m²)	Relative irradiated power
10	1165	1
5	700	0.6
2.5	407	0.35
1	203	0.17

Mixed hetero-/homogeneous TiO₂/N-hydroxyimide photocatalysis in visible-light-induced controllable benzylic oxidation by molecular oxygen

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Run	Deviation from general conditions ^a	X (%)	S_2a (%)	S_3a (%)	S_4a (%)
1	None	40	39	5	48
1	None	(43)	(40)		(44)
2	TiO₂without NHPI	—	—	—	—
3	NHPI without TiO₂	<5	80	—	—
4	TiO₂ was filtered before irradiation	<5	76	—	—
5	No irradiation (in dark)	<5	50	—	—
6	Irradiation by 10 W violet LED (λ_max = 405 nm)	44	22	6	65
7	Irradiation by 10 W UV LED (λ_max = 373 nm)	27	51	4	28
12	5 W blue LED	39	44	3	45
12	5 W blue LED	(41)	(44)		(49)
13	1 W blue LED	31	55	3	32
14	NHSI instead of NHPI	21	8	9	28
15	Cl₄-NHPI instead of NHPI	28	40	8	52
16	NHNPI instead of NHPI	26	3	11	53
17	TiO₂ anatase nanopowder	25	62	4	21
18	TiO₂ P25 Aeroxide	26	59	5	24
19	C₂H₄Cl₂ as solvent	19	14	5	70
20	PhCl as solvent	13	6	8	85
20	PhCl as solvent	(18)	(13)		(60)
21	MeNO₂ as solvent	57	12	9	75
22	AcOH as solvent	(33)	(17)		(48)
23	40 °C	55	15	4	66
23	40 °C	(56)	(18)		(60)
24	60 °C	66	2	2	85
25	Reaction under air	32	29	4	59
26	Reaction under argon	<5	—	—	87
27	Reaction time 24 h	65	4	2	85

Run	NHPI (mol%)	TiO₂ (mg)	X (%)	S_2a (%)	S_3a (%)	S_4a (%)
1	10	10	40	39	5	48
2	10	5	36	54	5	35
3	10	2.5	31	67	3	23
4 ^b	10	2.5	13	90	—	2
5 ^c	10	2.5	18	79	—	16
6 ^d	10	2.5	37	55	5	37
7 ^e	40	2.5	32	76	—	15
8 ^e	10	10	30	34	6	49
8 ^e	10	10	(31)	(39)		(53)
9	5	10	28	28	6	62
10	2.5	10	24	14	6	67
11	10	20	43	23	4	67
12	10	40	44	19	5	71

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