PPh3衍生准多孔有机笼在Rh/PPh3体系催化氢甲酰化反应中的应用: 增强活性和选择性及可回收利用

doi:10.1016/S1872-2067(20)63746-9

催化学报 ›› 2021, Vol. 42 ›› Issue (7): 1216-1226.DOI: 10.1016/S1872-2067(20)63746-9

PPh₃衍生准多孔有机笼在Rh/PPh₃体系催化氢甲酰化反应中的应用: 增强活性和选择性及可回收利用

汪文龙^b^,†, 李存耀^a^,†, 张恒^c^,†, 张江威^a, 卢兰露^d, 姜政^d^,^e, 崔立峰^b, 刘宏光^c^,^#(), 严丽^a^,^$(), 丁云杰^a^,^*()

^a中国科学院大连化学物理研究所, 洁净能源国家实验室(筹), 催化基础国家重点实验室, 辽宁大连116023
^b东莞理工学院材料科学与工程学院, 广东东莞523808
^c暨南大学化学与材料学院, 广东暨南510632
^d中国科学院上海高等研究院, 上海210210
^e中国科学院上海应用物理研究所, 上海同步辐射光源, 上海201204

收稿日期:2020-10-22 接受日期:2020-11-25 出版日期:2021-07-18 发布日期:2020-12-10
通讯作者: 刘宏光,严丽,丁云杰
作者简介:
^†共同第一作者.
基金资助:
中国科学院战略性先导科技专项(XDA21020300);中国科学院战略性先导科技专项(XDB17020400);国家重点研发计划(2017YFB0602203);国家自然科学基金(21972018);东莞理工学院新能源材料研究中心(KCYCXPT2017005);东莞理工学院科研启动基金(KCYKYQD2017015)

Enhancing the activity, selectivity, and recyclability of Rh/PPh₃ system-catalyzed hydroformylation reactions through the development of a PPh₃-derived quasi-porous organic cage as a ligand

Wenlong Wang^b^,†, Cunyao Li^a^,†, Heng Zhang^c^,†, Jiangwei Zhang^a, Lanlu Lu^d, Zheng Jiang^d^,^e, Lifeng Cui^b, Hongguang Liu^c^,^#(), Li Yan^a^,^$(), Yunjie Ding^a^,^*()

^aDalian National Laboratory for Clean Energy, and State Key Laboratory of catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^bSchool of Materials Science and Engineering, Dongguan University of Technology, Dongguan 523808, Guangdong, China
^cCollege of Chemistry and Materials Science, Jinan University, Guangzhou 510632, Guangdong, China
^dShanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201210, China
^eShanghai Synchrotron Radiation Facility, Shanghai Institute of Applied Physics, Chinese Academy of Sciences, Shanghai 201204, China

Received:2020-10-22 Accepted:2020-11-25 Online:2021-07-18 Published:2020-12-10
Contact: Hongguang Liu,Li Yan,Yunjie Ding
About author:^$ Tel/Fax: +86-411-84379143; E-mail: yanli@dicp.ac.cn
^# Tel: +86-15602302185; E-mail: hongguang_liu@jnu.edu.cn;
^* Tel/Fax: +86-411-84379143; E-mail: dyj@dicp.ac.cn;
First author contact:
^† These authors contributed equally to this work.
Supported by:
Strategic Priority Research Program of the Chinese Academy of Sciences(XDA21020300);Strategic Priority Research Program of the Chinese Academy of Sciences(XDB17020400);National Key R&D Program of China(2017YFB0602203);National Natural Science Foundation of China(21972018);Dongguan University of Technology (DGUT) Research Center of New Energy Materials(KCYCXPT2017005);the Startup Research Fund of DGUT(KCYKYQD2017015)

摘要/Abstract

摘要：

多孔有机笼(POCs)由英国利物浦大学的Cooper教授在2009年首次合成, 这种多孔小分子材料的出现具有两方面重要意义: (1)开拓了多孔材料领域的一个全新分支, 改变了人们对多孔材料的传统认知; (2)由于POCs材料由离散的小分子堆积而成, 可溶解于一些常用的有机溶剂中, 因此其在材料制备方面具有很好的“溶液成型”性能, 该优势是三维延伸网状多孔材料所不具备的. POCs本质上是一种“中心带孔”的有机小分子, 由刚性有机分子砌块收敛堆叠而成, 其特殊结构在气体吸附与分离等方面表现出很好的应用前景. 不同于传统空间延伸网状框架材料(如金属-有机框架材料和共价有机框架材料)及多孔有机聚合物(POPs)材料, POCs是一种在大多数有机溶剂中可溶解的小分子材料, 因此在均相催化领域也有很好的应用前景.
作为最为经典的有机配体, 三苯基膦(PPh₃)在金属有机化学和均相催化领域应用十分广泛, 如目前均相催化工业应用最成功的典范之一氢甲酰化反应, 大多数情况下使用的是PPh₃与Rh形成的络合物催化剂. 本文首先将PPh₃进行醛基官能团化, 通过醛基和氨基的收敛缩合形成POCs材料, 合成了基于PPh₃配体的准多孔有机笼(POC-DICP), 利用得到的多孔有机笼制备出类Rh/PPh₃均相催化体系的Rh/POC-DICP络合催化体系, 并将其应用于氢甲酰化反应. 相比于经典的Rh/PPh₃均相催化体系, 该Rh/POC-DICP催化体系在氢甲酰化反应中不仅展示出了更高的活性和目标产物醛的选择性(醛的化学选择性为97%, 醛的正异构比为1.89), 而且可以很方便地从均相反应体系中沉淀回收(通过调整溶剂体系极性). 在氢甲酰化反应中, Rh/POC-DICP体系显示出了良好的底物适用性, 在己烯、庚烯、辛烯和苯乙烯的氢甲酰化反应中均表现出良好的催化活性和醛选择性, 同时催化剂回收使用4次, 未见催化性能明显下降. X射线单晶衍射、同步辐射及DFT计算等结果表明, Rh/POC-DICP催化体系在氢甲酰化反应中具有较高活性和选择性的原因是POC-DICP多孔有机笼分子的有利的空间咬合角(123.88^o)和P原子上相对的缺电子效应.
本文设计合成的PPh₃衍生的多孔有机笼不仅拓宽了多孔有机笼材料在催化领域的应用, 而且为新型配体及络合催化剂的设计、合成及修饰提供了新的思路.

关键词: 氢甲酰化反应, 三苯基膦, 多孔有机笼, 化学选择性, 线性-区域选择性

Abstract:

In contrast to heterogeneous network frameworks (e.g., covalent organic frameworks and metal-organic frameworks) and porous organic polymers, porous organic cages (POCs) are soluble molecules in common organic solvents that provide significant potential for homogeneous catalysis. Herein, we report a triphenylphosphine-derived quasi-porous organic cage (denoted as POC-DICP) as an efficient organic molecular cage ligand for Rh/PPh₃ system-catalyzed homogeneous hydroformylation reactions. POC-DICP not only displays enhanced hydroformylation selectivity (aldehyde selectivity as high as 97% and a linear-to-branch ratio as high as 1.89) but can also be recovered and reused via a simple precipitation method in homogeneous reaction systems. We speculate that the reason for the high activity and good selectivity is the favorable geometry (cone angle = 123.88°) and electronic effect (P site is relatively electron-deficient) of POC-DICP, which were also demonstrated by density functional theory calculations and X-ray absorption fine-structure characterization.

Key words: Hydroformylation, Triphenylphosphine, Porous organic cages, Chemical selectivity, Linear-regioselectivity

汪文龙, 李存耀, 张恒, 张江威, 卢兰露, 姜政, 崔立峰, 刘宏光, 严丽, 丁云杰. PPh₃衍生准多孔有机笼在Rh/PPh₃体系催化氢甲酰化反应中的应用: 增强活性和选择性及可回收利用[J]. 催化学报, 2021, 42(7): 1216-1226.

Wenlong Wang, Cunyao Li, Heng Zhang, Jiangwei Zhang, Lanlu Lu, Zheng Jiang, Lifeng Cui, Hongguang Liu, Li Yan, Yunjie Ding. Enhancing the activity, selectivity, and recyclability of Rh/PPh₃ system-catalyzed hydroformylation reactions through the development of a PPh₃-derived quasi-porous organic cage as a ligand[J]. Chinese Journal of Catalysis, 2021, 42(7): 1216-1226.

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图/表 13

Fig. 1. Famous Rh/PPh3 catalytic systems for hydroformylation reaction.

Fig. 2. (a) Synthesis of PPh3-derived POC by dynamic covalent synthesis; (b) single crystal structure determined by X-ray diffraction (for clarity, H atoms are omitted), CCDC number: 1857136.

Fig. 3. Morphological characterization of POC-DICP by helium ion microscopy. (a) Scale bar = 5 μm; (b) Scale bar = 2 μm; (c) Scale bar = 1 μm; (d) Scale bar = 200 nm.

Fig. 4. Nitrogen gas sorption isotherm at 77 K for cage POC-DICP.

Table 1 Hydroformylation of 1-octene employing different catalysts.

Entry	Cat.	Time (h)	S/C (× 1000)	Conv. (%)	Aldehyde sel.%	Alkane sel.%	Iso-alkene sel.%	TOF (h^‒1)	l/b
1	Rh/POC	1	12	97.8	59.8	2.8	37.4	7018	1.46
2	Rh/PPh₃	1	12	96.8	37.2	5.4	57.4	4321	0.99
3	Rh/POC	4	12	>99	88.9	2.6	8.5	2654	1.40
4	Rh/PPh₃	4	12	>99	53.3	5.2	41.6	1591	0.99
5	HRh(CO) (PPh₃)₃	4	12	>99	31.3	14.8	53.9	934	0.54
6	Rh/POC	4	6	>99	91.4	0.8	7.8	1364	1.88
7	Rh/PPh₃	4	6	>99	71.4	1.9	26.7	1066	1.10

Table 2 Comparison with other reported catalysts (substrate is 1-octene).

Entry	Catalyst	Conv. (%)	Aldehyde sel. (%)	TOF (h^‒1)	Ref.
1	Rh/POC-DICP	99.5	88.9	2654	—
2	Rh/dppe	99.5	52.3	416	[18]
3	Rh(CO)₂acac	98.8	50.1	396	[18]
4	Rh/POL-dppe	96.9	99.3	770	[18]

Table 3 Hydroformylation of diverse olefins employing Rh/POC-DICP catalyst.

Entry	Substrates	Conv. (%)	Selectivity (%)			l/b
Entry	Substrates	Conv. (%)	Aldehydes	Alkane	Iso-alkenes	l/b
1	1-octene	99.5	94.0	1.3	4.7	1.07
2	2-octene	90.9	89.8	3.2	7.0	0.17
3	1-hexene	99.9	97.3	0.5	2.2	1.89
4	1-heptene	95.0	94.0	0.9	5.1	1.39
5	Styrene	99.6	98.6	1.4	0	1.29
6 ^a	Propene	95.3	99.4	less	none	1.5

Table 4 Catalyst recycling data of hydroformylation reaction.

Reaction cycle	Conversion (%)	Aldehydes sel. (%)	Alkane sel. (%)	Iso-alkenes sel. (%)	l/b ratio
1	99.6	85.4	6.1	8.5	1.38
2	99.6	85.1	6.2	8.7	1.41
3	99.6	86.0	5.8	8.2	1.40
4	99.6	86.1	5.8	8.1	1.40
5	99.6	85.9	5.9	8.2	1.43

Fig. 5. IR diagrams of the complexes POC-DICP-Ni(CO)3 and PPh3-Ni(CO)3.

Fig. 6. Cone angles of POC-DICP and PPh3.

Fig. 7. EXAFS fitting spectra (a) and its corresponding interpretation of coordination modes (b).

Fig. 8. Transition states of Rh-catalyzed hydroformylation reaction, and the energy comparison diagrams of two parallel paths of linear and branch aldehydes.

Fig. 9. Proposed hydroformylation cycle of linear aldehyde catalyzed by a single P cage-coordinated Rh catalyst.

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PPh₃衍生准多孔有机笼在Rh/PPh₃体系催化氢甲酰化反应中的应用: 增强活性和选择性及可回收利用

Enhancing the activity, selectivity, and recyclability of Rh/PPh₃ system-catalyzed hydroformylation reactions through the development of a PPh₃-derived quasi-porous organic cage as a ligand

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