Pd loaded TiO2 as recyclable catalyst for benzophenone synthesis by coupling benzaldehyde with iodobenzene under UV light

doi:10.1016/S1872-2067(23)64616-9

Abstract

Abstract:

The benzophenone structural unit is one of the most important functional groups in organic chemistry, which has a wide range of applications in drugs, light-curing agent, UV-light absorbent and so on. However, the traditional synthetic methods of benzophenone generally involve additives or toxic regents, leading to a large amount of waste and non-recyclable of [Pd] catalyst. Herein, we report Pd loaded carbon-modified TiO₂ (Pd/C-TiO₂) as an efficient and recyclable catalyst realized the generation of benzophenone through cross-coupling of benzaldehyde and iodobenzene under UV light irradiation, with the yield of 98% and selectivity up to 99%. Based on density functional theory (DFT) calculation and electron paramagnetic resonance (EPR) analysis, the reaction undergoes the Pd⁰-Pd^II-Pd^III catalytic pathway, that is, benzaldehyde directly activated to acyl radical under UV light and then attracted by Pd-iodobenzene complex to proceed the coupling reaction for benzophenone generation. Owing to the in-situ reduction of dissolved [Pd] through TiO₂ photocatalyst in the reaction system, good recyclability of metallic Pd can be achieved. This work not only shed light on a facile method for the synthesis of carbonyl-containing compounds but also offered a practical approach for minimizing the leaching of active metals in transition metal-catalyzed coupling reactions.

Key words: Pd/C-TiO₂, Heterogeneous catalysis, Cross-coupling of benzaldehyde and iodobenzene, Benzophenone synthesis, Photocatalytic Pd recycling

Yang Li, Xiong Wang, Xing-Sheng Hu, Biao Hu, Sheng Tian, Bing-Hao Wang, Lang Chen, Guang-Hui Chen, Chao Peng, Sheng Shen, Shuang-Feng Yin. Pd loaded TiO₂ as recyclable catalyst for benzophenone synthesis by coupling benzaldehyde with iodobenzene under UV light[J]. Chinese Journal of Catalysis, 2024, 59: 159-168.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64616-9

https://www.cjcatal.com/EN/Y2024/V59/I4/159

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Entry	Catalyst	Condition	Time (h)	Yield (%)	Ref.
1	Co₃O₄/Ag@C₃N₄	hv, r.t.	5	71	[2]
2	Fe₂O₃	r.t.	0.25	95	[52]
3	Nano-SiO₂@CoCl₃-C12IL	100 °C	8	89	[53]
4	NiO	r.t.	2	91	[54]
5	SiO₂-Si-SCF₃	80 °C	12	93	[55]
6	(Cu₁Pd₂)_1.3@PCN-222(Co)	hv, r.t.	5	90	[8]
7	Pd/fibrous nanosilica	100 °C	6	99	[9]
8	Ni@Pd/CNT	150 °C	0.5	98	[56]
9	Pd/g-C₃N₄	100 °C	16	61	[57]
10	SBA-16/DFMP-Pd	80 °C	0.25	94	[58]
11	0.85-Pd/C-TiO₂	hv, r.t.	10	98	This work

Entry	Catalyst	Condition	Time (h)	Yield (%)	Ref.
1	Co₃O₄/Ag@C₃N₄	hv, r.t.	5	71	[2]
2	Fe₂O₃	r.t.	0.25	95	[52]
3	Nano-SiO₂@CoCl₃-C12IL	100 °C	8	89	[53]
4	NiO	r.t.	2	91	[54]
5	SiO₂-Si-SCF₃	80 °C	12	93	[55]
6	(Cu₁Pd₂)_1.3@PCN-222(Co)	hv, r.t.	5	90	[8]
7	Pd/fibrous nanosilica	100 °C	6	99	[9]
8	Ni@Pd/CNT	150 °C	0.5	98	[56]
9	Pd/g-C₃N₄	100 °C	16	61	[57]
10	SBA-16/DFMP-Pd	80 °C	0.25	94	[58]
11	0.85-Pd/C-TiO₂	hv, r.t.	10	98	This work

Pd loaded TiO₂ as recyclable catalyst for benzophenone synthesis by coupling benzaldehyde with iodobenzene under UV light

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Entry	Variations from indicated condition	Conversion of B1^a (%)	Yield^a (%)
Entry	Variations from indicated condition	Conversion of B1^a (%)	C1	D1
1	no variation	87	86	1
2	C-TiO₂ instead of 0.85-Pd/C-TiO₂	0	0	0
3	commercial TiO₂ instead of 0.85-Pd/C-TiO₂ Pd/commercial TiO₂	0	0	0
4 ^b		70	66	4
5^b	Pd(OAc)₂ instead of 0.85-Pd/C-TiO₂	83	83	0
6^b	Pd/SiO₂	85	85	0
7^b	Pd/Al₂O₃	82	82	0
8	without Na₂CO₃	8	8	0
9	1 equiv. Na₂CO₃	60	58	2
10	NaHCO₃ instead of Na₂CO₃	58	55	3
11	K₂CO₃ instead of Na₂CO₃	80	77	3
12	Cs₂CO₃ instead of Na₂CO₃	72	8	64
13	A1 (0.2 mmol)	21	16	5
14	A1 (0.6 mmol)	47	46	1
15	in air	trace	trace	trace
16	methanol instead of acetonitrile	>99	0	>99
17	acetone instead of acetonitrile	55	50	5
18	in dark	0	0	0
19	at 323 or 373 K without irradiation	0	0	0
20	Xenon lamp with 350 nm bandpass filter	49	49	0
21	Xenon lamp with 365 nm bandpass filter	28	27	1
22	λ ≧ 400 nm	0	0	0
23	λ ≧ 420 nm	0	0	0

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