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

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

Chinese Journal of Catalysis ›› 2021, Vol. 42 ›› Issue (7): 1216-1226.DOI: 10.1016/S1872-2067(20)63746-9

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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)

Abstract

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

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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Figures/Tables 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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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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