可循环Pd/TiO2构筑及其紫外光催化苯甲醛与碘苯偶联合成二苯甲酮

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

催化学报 ›› 2024, Vol. 59: 159-168.DOI: 10.1016/S1872-2067(23)64616-9

可循环Pd/TiO₂构筑及其紫外光催化苯甲醛与碘苯偶联合成二苯甲酮

李洋, 王雄, 胡星盛, 胡彪, 田昇, 王丙昊, 陈浪(), 陈广辉, 彭超, 申升(), 尹双凤()

湖南大学化学化工学院, 先进催化教育部工程研究中心, 化学生物传感与计量学国家重点实验室, 湖南长沙 410082

收稿日期:2023-11-05 接受日期:2024-01-24 出版日期:2024-04-18 发布日期:2024-04-15
通讯作者: *电子信箱: huagong042cl@163.com (陈浪), sshen@hnu.edu.cn (申升), sf_yin@hnu.edu.cn (尹双凤).
基金资助:
国家重点研发计划(2022YFB4002400);国家自然科学基金(22278119);国家自然科学基金(21938002);国家自然科学基金(22322804);国家自然科学基金(21975069)

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

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()

Advanced Catalytic Engineering Research Center of the Ministry of Education, State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, Hunan, China

Received:2023-11-05 Accepted:2024-01-24 Online:2024-04-18 Published:2024-04-15
Contact: *E-mail: huagong042cl@163.com (L. Chen), sshen@hnu.edu.cn (S. Shen), sf_yin@hnu.edu.cn (S.-F. Yin).
Supported by:
The National Key Research and Development Program of China(2022YFB4002400);The National Natural Science Foundation of China(22278119);The National Natural Science Foundation of China(21938002);The National Natural Science Foundation of China(22322804);The National Natural Science Foundation of China(21975069)

摘要/Abstract

摘要：

二苯甲酮是有机化学中最重要的结构单元之一, 广泛存在于药物、香料、光敏剂以及许多天然产物中. 然而, 传统的二苯甲酮合成方法通常涉及添加剂或有毒试剂, 且产生大量废弃物, 不利于环保. 苯甲醛与卤代苯的直接偶联反应因原料易得而备受关注, 但苯甲醛C(sp²)-H键的高键能(371 kJ mol^-1)导致其活化困难, 反应条件苛刻. 此外, 常用的Ni或Pd均相催化剂在反应体系中难以分离回收, 限制了其应用. 因此, 构筑多相可回收催化剂成为研究热点. 将活性钯金属负载到多相载体上进行酮合成, 可以解决催化剂回收问题, 但活性金属钯的浸出仍是挑战. 本研究旨在探索制备有效的多相可回收催化剂, 以推动二苯甲酮的环保合成.

本文通过煅烧Pd²⁺/MIL-125-NH₂制备了碳修饰二氧化钛负载的钯纳米颗粒(Pd/C-TiO₂), 这是一种高效且可回收的多相催化剂. 在紫外光照射下, 该催化剂能有效催化苯甲醛和碘苯偶联合成二苯甲酮. 研究结果表明, 苯甲醛活化是该反应过程的控速步骤, 而紫外光诱导生成的酰基自由基则是反应进行的关键. 在不添加强氧化剂和配体的情况下, 二苯甲酮的产率最高可达98%, 选择性高达99%. 通过电子顺磁共振技术检测到, 反应过程中苯甲醛和碘苯均有可能生成碳自由基. 利用密度泛函理论计算研究了基于碳自由基生成二苯甲酮的两种可能发生的路径, 结果表明, 相较于Pd⁰-Pd^I-Pd^III过程(苯自由基进攻醛基自由基与钯加成的复合物), 该反应更有可能通过Pd⁰-Pd^II-Pd^III催化路径发生, 即苯甲醛在紫外光下直接活化生成酰基自由基, 然后进攻碘苯与钯氧化加成的复合物, 最终通过还原消除生成二苯甲酮. 醋酸钯、Pd/SiO₂催化剂等一系列对照试验结果表明, 钯在反应体系中首先溶解并参与反应, 随后在紫外光照射下被二氧化钛光催化剂原位还原, 从而实现金属钯的原位沉积, 有效抑制了钯金属的流失. 催化剂在循环使用10次后, 其活性没有明显下降.

综上所述, 本文利用高能紫外光直接活化苯甲醛与TiO₂光催化剂的高氧化还原性能相匹配, 实现了紫外光下苯甲醛与碘苯偶联制备二苯甲酮和Pd催化剂的高效回收利用. 本研究为在紫外光下活化苯甲醛与其他化合物偶联合成含羰基化合物提供了一种简便的方法, 并为设计有机反应中可回收的钯催化剂提供了参考.

关键词: 钯, 碳修饰二氧化钛, 多相催化, 苯甲醛与碘苯的交叉偶联, 二苯甲酮的合成, 光催化钯回收

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

李洋, 王雄, 胡星盛, 胡彪, 田昇, 王丙昊, 陈浪, 陈广辉, 彭超, 申升, 尹双凤. 可循环Pd/TiO₂构筑及其紫外光催化苯甲醛与碘苯偶联合成二苯甲酮[J]. 催化学报, 2024, 59: 159-168.

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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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

可循环Pd/TiO₂构筑及其紫外光催化苯甲醛与碘苯偶联合成二苯甲酮

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

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Metrics

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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