功能化聚丙烯腈纤维促进有机反应的研究进展

doi:10.6023/cjoc202209003

摘要/Abstract

聚丙烯腈纤维(PANF)具有出色的机械强度、耐化学性和良好的热稳定性, 而且易于进行改性. 在聚丙烯腈纺丝原液中加入添加剂或功能单体, 或对PANF进行热处理等方法可以实现物理改性. 而PANF的化学表面改性包括胺化、酰胺化、氧化、还原、交联、水解、酸处理和化学枝接等方法, 表面改性给PANF带来许多特殊官能团, 使其可以进一步被用作有机物、有机配体、酶以及过渡金属的载体. 通过负载催化活性位点从而得到具有催化活性的功能化PANF. 近年功能化PANF作为非均相催化剂被广泛应用于有机合成领域, 综述了功能化PANF催化剂在有机反应中的研究成果与进展, 包括缩合反应、偶联反应、加成反应、氧化还原反应及多组分一锅法反应等. 介绍了纤维催化剂的合成及结构, 讨论了催化性能, 分析了可能的催化机理, 为开发更优的功能化PANF做铺垫.

关键词: 聚丙烯腈纤维, 载体, 改性, 功能化, 催化, 有机合成

Polyacrylonitrile fiber (PANF) has excellent mechanical strength, chemical resistance and good thermal stability, and it is easy to be modified. Physical modification can be achieved by adding additives or functional monomers into polyacrylonitrile spinning dope or heat treating PANF. Chemical surface modification of PANF includes amination, amidation, oxidation, reduction, cross-linking, hydrolysis, acid treatment and chemical grafting. Surface modification brings many special functional groups to PANF, which can be further used as carriers of organic compounds, organic ligands, enzymes and transition metals. Functionalized PANF with catalytic activity was obtained by loading the catalytic active sites. In recent years, functional PANF has been widely used as heterogeneous catalyst in the field of organic synthesis. The research achievements and progress of functional PANF catalyst in organic reactions are reviewed, including condensation reaction, coupling reaction, addition reaction, redox reaction and multi-component one-pot reaction. The synthesis and structure of fiber catalyst are introduced, the catalytic performance is discussed, and the possible catalytic mechanism is analyzed, which pave the way for the development of better functional PANF.

Key words: polyacrylonitrile fiber, carrier, modification, functionalization, catalysis, organic synthesis

引用此文

白林盛, 洪鹏, 应安国. 功能化聚丙烯腈纤维促进有机反应的研究进展[J]. 有机化学, 2023, 43(4): 1241-1270.

Linsheng Bai, Peng Hong, Anguo Ying. Research Progress of Functional Polyacrylonitrile Fiber in Promoting Organic Reaction[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1241-1270.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 25

图式1. Doebner-Knoevenagel反应可能的协同催化机理

Scheme 1. Possible cooperative catalytic mechanism of the Doebner-Knoevenagel reaction

图式2. PANEPF催化Aldol反应可能的机理

Scheme 2. Possible mechanism of Aldol reaction catalyzed by PANEPF

Entry	Fiber	Retention strength/cN	Retention of breaking strength^a/%
1	PANF	11.0	100
2	C-PANF-Na	8.1	73
3	C-PANF-Na-1	8.1	73
4	C-PANF-Na-18	7.9	72

表1. PANF、C-PANF-Na、C-PANF-Na-1和C-PANF-Na-18的机械性能

Table 1. Mechanical properties of PANF, C-PANF-Na, C- PANF-Na-1 and C-PANF-Na-18

图式3. PANGQAF-Pd(0)催化Heck反应的可能机理

Scheme 3. Possible mechanism for PANGQAF-Pd(0) catalyzed Heck reaction

Entry	Catalyst	Catalyst amount/mol%	Rection condition	Yield^a/%	Reuse time	Ref
1	AOFs-Pd(0)	0.8	DMF, 110 ℃, 3 h	95.5	3	[117]
2	Pd(PNODAM-5)	2.0	Heptane, 100 ℃, 22 h	96	3	[118]
3	Pd/APS-MIL-101	0.93	DMF, 120 ℃, 1 h	97	—	[119]
4	FeO₃O₄@PCA/Pd(0)-b-PEG	0.05	H₂O, 90 ℃, 2 h	98	10	[120]
5	PdNPore	2.0	MeOH, 80 ℃, 18 h	94	5	[121]
6	Pd-MPTAT-1	0.97	H₂O/EtOH (V∶V=1∶1), reflux, 6 h	95	2	[122]
7	Pd-SP-CMP	0.6	1,4-Dioxane/H₂O (V∶V=1∶1), 80 ℃, 12 h	99	—	[123]
8	Pd@IPN	0.0229	H₂O, 100 ℃, 12 h	96	11	[124]
9	PAN_PhenF-Pd(0)	0.1	Solvent-free, 110 ℃, 3 h	97	6	[54]

表2. 不同催化体系下碘苯和丙烯酸的Heck反应的比较

Table 2. Comparison of the Heck reaction of iodobenzene and acrylic with different catalytic systems

图式4. Pd NPs/PCNFs催化剂的制备示意图[61]

Scheme 4. Schematic of the preparation of Pd NPs/PCNFs catalyst[61]

图式5. Pd NPs/PAN催化剂的制备示意图[66]

Scheme 5. Schematic of the preparation of Pd NPs/PAN catalyst[66]

图式6. PANF-NHC-Ag催化A3偶联反应的机理

Scheme 6. Mechanism of A3 coupling reaction catalyzed by PANF-NHC-Ag

Entry	Catalyst	Rection condition	Yield^a/%	Reuse time	Ref.
1	SiO₂-NHC-Cu	MeOH, 50 ℃, 3 h	90	6	[125]
2	Ps-Cu	MeOH, 40 ℃, 10 h	99	5	[126]
3	Cu@PI-COF	MeOH-H₂O, r.t., 8 h	87	8	[127]
4	Cu-(tpa)MOF	EtOH, Et₃N, r.t., 12 h	99	5	[128]
5	Cu₃(BTC)₂	EtOH, Et₃N, 60 ℃, 12 h	92	4	[129]
6	Cu-doped CoFe₂O₄	MeOH, Et₃N, r.t., 5 h	92	7	[130]
7	URJC-1-MOF	DMF, K₂CO₃, r.t., 15 h	61	5	[131]
8	CuO NPs	MeOH-H₂O, r.t., 10 h	88	6	[132]
9	CuCl₂@PAN_PA-2F	MeOH, 60 ℃, 3 h	98	5	[80]

表3. 合成N-苯基咪唑的Chan-Lam偶联反应中不同催化体系的比较

Table 3. Comparison of different catalytic system in Chan-Lam coupling reaction for the synthesis of N-phenylimidazole

图式7. 连续流动过程的示意图[81]

Scheme 7. Schematic representation of the continuous-flow process[81]

图式8. PANp-AP-3F催化Gewald反应的可能机理

Scheme 8. Possible mechanism for the Gewald reaction catalyzed by PANp-AP-3F

图式9. CO2与环氧化物环加成反应的可能机理

Scheme 9. Possible mechanism of the cycloaddition of CO2 with epoxides

Entry	Fiber	Retention strength/cN	Retention of breaking strength^a/%
1	PANF	10.56	100
2	PANF-CEIMBr	7.93	75.1
3	PANF-CEIMBr-1	7.91	74.9
4	PANF-CEIMBr-21	7.64	72.3

表4. PANF、PANF-CEIMBr、PANF-CEIMBr-1和PANF- CEIMBr-21的机械性能

Table 4. Mechanical Properties of PANF, PANF-CEIMBr, PANF-CEIMBr-1 and PANF-CEIMBr-21

图1. PANF-QAS中季铵盐负载的两种模式

Figure 1. Two modes of quaternary ammonium salt loading in PANF-QAS

图式10. PANF@SPA&VImPW的转化机理

Scheme 10. Conversion mechanism of the PANF@SPA&VImPW

图式11. Ag NPs/CNFs的制备工艺流程图[100]

Scheme 11. Scheme of the Ag NPs/CNFs preparation process[100]

图式12. Pd@MPTMS@ZnO@PAN-NF的制备工艺流程图[102]

Scheme 12. Scheme of the Pd@MPTMS@ZnO@PAN-NF preparation process[102]

图式13. PANGQAF-Pd(0)催化还原4-硝基苯酚

Scheme 13. PANGQAF-Pd(0) catalyzed reduction of 4-nitro- phenol

图式14. 制备2-氨基-4H-色烯的可能机理

Scheme 14. Possible mechanism for the preparation of 2-amino-4H-chromene

图式15. 可能的“释放和捕获”催化过程

Scheme 15. Possible “release and catch” catalytic process

图式16. 基于PANF表面静电微环境可能的“释放-捕获-释放-捕获”催化模式

Scheme16. Possible “release-catch-release-catch” catalytic pattern based on the electrostatic microenvironment of PANF surface

图式17. 可能的“微环境促进”催化过程

Scheme 17. Possible “micro-environment promote” catalytic process

图式18. EIMBr-PANFTA@CuI催化羧化反应的可能机理

Scheme18. Possible mechanism for the carboxylation catalyzed by EIMBr-PANFTA@CuI

图2. 叶轮中带有纤维催化剂的旋转篮式反应器的示意图[114]

Figure 2. A diagrammatic sketch of the spinning basket reactor with the fiber catalyst in the impellers[114]

Entry	Active center species	Catalyst
1	Tertiary amine group	1a~1b, 5, 8, 16, 48, 52a~52b
2	Secondary amine group	6
3	Proline amides	3, 12
4	Aminopyridine group	7, 10, 33, 38b~38d, 46a~46b, 47
5	Chiral pyrrolidine	34
6	Phosphoric acid group	45, 51
7	Proline group	4, 11
8	L-Lysine	9
9	Sulfonic acid group	17
10	Phosphotungstic acid	4, 50
11	Quaternary ammonium group	13, 14, 35, 37, 41, 49
12	Imidazole ionic liquid	36a~36e
13	Supported metal Cu	21, 28, 30, 31, 39, 53
14	Pd nanoparticles	19, 23
15	Pd complex	20, 22
16	Doping Pd	25
17	Ag complex	26
18	Ag nanoparticles	32
19	Supported metal Au	27, 42
20	Ni complex	29
21	Fe complex	44, 54

表5. 催化活性中心的种类

Table 5. Types of catalytic active centers

参考文献 132

[1]	Xu, G.; Wang, L.; Li, M. M.; Tao, M. L.; Zhang, W. Q. Green Chem. 2017, 19, 5818. doi: 10.1039/C7GC02935G
[2]	Cole-Hamilton, D. J. Science 2003, 299, 1702. pmid: 12637737
[3]	Wang, X. L.; Yang, M.; Zhu, L. J.; Zhu, X. N.; Wang, S. R. J. Fuel Chem. Technol. 2020, 48, 456. doi: 10.1016/S1872-5813(20)30020-7
[4]	Gogoi, P.; Dutta, A. K.; Saikia, S.; Borah, R. Appl. Catal., A 2016, 523, 321. doi: 10.1016/j.apcata.2016.06.015
[5]	Schulze, J. S.; Migenda, J.; Becker, M.; Schuler, S. M.; Wende, R. C.; Schreiner, P. R.; Smarsly, B. M. J. Mater. Chem. A 2020, 8, 4107. doi: 10.1039/C9TA12416K
[6]	Liu, G. H.; Zong, Z. M.; Liu, Z. Q.; Liu, F. J.; Zhang, Y. Y.; Wei, X. Y. Fuel Process Technol. 2018, 179, 114. doi: 10.1016/j.fuproc.2018.05.035
[7]	Pan, S.; Yan, S.; Osako, T.; Uozumi, Y. ACS Sustainable Chem. Eng. 2017, 5, 10722. doi: 10.1021/acssuschemeng.7b02646
[8]	Baran, T. J. Mol. Struct. 2017, 1141, 535. doi: 10.1016/j.molstruc.2017.03.122
[9]	Lu, X. T.; Li, S. N.; Wang, L. M.; Huang, S. J.; Liu, Z. Q.; Liu, Y. J.; Ying, A. G. Fuel 2022, 310, 122318. doi: 10.1016/j.fuel.2021.122318
[10]	Badoga, S.; Sohani, K.; Zheng, Y.; Dalai, A. K. Fuel Process. Technol. 2017, 168, 140. doi: 10.1016/j.fuproc.2017.08.033
[11]	McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. doi: 10.1021/cr0103571
[12]	Zheng, Y. W.; Zhao, W.; Jia, D.; Cui, L.; Liu, J. Q. Chem. Eng. J. 2019, 364, 70. doi: 10.1016/j.cej.2019.01.076
[13]	Zhang, Y. Y.; Sun, Y. L.; Peng, L. F.; Yang, J. Q.; Jia, H. H.; Zhang, Z. R.; Shan, B.; Xie, J. Energy Storage Mater. 2019, 21, 287.
[14]	Xiao, J.; Wang, L.; Ran, J. R.; Zhao, J. Y.; Tao, M. L.; Zhang, W. Q. React. Funct. Polym. 2020, 146, 104394. doi: 10.1016/j.reactfunctpolym.2019.104394
[15]	Xu, G.; Xu, W. S.; Tian, S.; Zheng, W. J.; Yang, T.; Wu, Y. X.; Xiong, Q. Z.; Kalkhajeh, Y. K.; Gao, H. J. Chem. Eng. J. 2021, 416, 127889. doi: 10.1016/j.cej.2020.127889
[16]	Xing, X. L.; Yang, H. X.; Tao, M. L.; Zhang, W. Q. J. Hazard. Mater. 2015, 297, 207. doi: 10.1016/j.jhazmat.2015.05.001
[17]	Li, Y.; Abedalwafa, M. A.; Ni, C. F.; Sanbhal, N.; Wang, L. React. Funct. Polym. 2019, 138, 18. doi: 10.1016/j.reactfunctpolym.2019.02.009
[18]	Hong, P.; Wang, L. M.; Bai, L. S.; Liu, Z. Q.; Liu, Y. J.; Yang J. G., Ying, A. G. Dyes Pigm. 2022, 197, 109902. doi: 10.1016/j.dyepig.2021.109902
[19]	Liu, X. M.; Li, M. Y.; Han, G. Y.; Dong, J. H. Electrochim. Acta 2010, 55, 2983. doi: 10.1016/j.electacta.2010.01.014
[20]	Shi, X. L.; Xing, X. L.; Lin, H. K.; Zhang, W. Q. Adv. Synth. Catal. 2014, 356, 2349. doi: 10.1002/adsc.v356.10
[21]	Xu, C. Z.; Du, J. G.; Ma, L. C.; Li, G. W.; Tao, M. L.; Zhang, W. Q. Tetrahedron 2013, 69, 4749. doi: 10.1016/j.tet.2013.02.084
[22]	Liu, R. X.; Zhang, B. W.; Tang, H. X. React. Funct. Polym. 1999, 39, 71. doi: 10.1016/S1381-5148(97)00174-0
[23]	Moroi, G.; Bilba, D.; Bilba, N. Polym. Degrad. Stab. 2004, 84, 207. doi: 10.1016/j.polymdegradstab.2003.10.013
[24]	Xiao, J.; Xu, G.; Wang, L.; Li, P. Y.; Zhang, W. Q.; Ma, N.; Tao, M. L. J. Ind. Eng. Chem. 2019, 77, 65. doi: 10.1016/j.jiec.2019.04.001
[25]	Li, G. W.; Xiao, J.; Zhang, W. Q. Dyes Pigm. 2012, 92, 1091. doi: 10.1016/j.dyepig.2011.08.015
[26]	Zheng, L. S.; Li, P. Y.; Tao, M. L.; Zhang, W. Q. Catal. Commun. 2019, 118, 19. doi: 10.1016/j.catcom.2018.09.009
[27]	Polander, L. E.; Barlow, S.; Seifried, B. M.; Marder, S. R. J. Org. Chem. 2012, 77, 9426. doi: 10.1021/jo301876v pmid: 23030064
[28]	Kudirka, R. A.; Barfield, R. M.; McFarland, J. M.; Drake, P. M.; Carlson, A.; Bañas, S.; Zmolek, W.; Garofalo, A. W.; Rabuka, D. ACS Med. Chem. Lett. 2016, 7, 994. pmid: 27882197
[29]	Liang, F. S.; Pu, Y. J.; Kurata, T.; Kido, J. J.; Nishide, H. Polymer 2005, 46, 3767. doi: 10.1016/j.polymer.2005.03.036
[30]	Zhu, H.; Xu, G.; Du, H. M.; Zhang, C. L.; Ma, N.; Zhang, W. Q. J. Catal. 2019, 374, 217. doi: 10.1016/j.jcat.2019.04.040
[31]	Li, G. W.; Xiao, J.; Zhang, W. Q. Chin. Chem. Lett. 2013, 24, 52. doi: 10.1016/j.cclet.2012.12.007
[32]	Li, G. W.; Xiao, J.; Zhang, W. Q. Green Chem. 2011, 13, 1828. doi: 10.1039/c0gc00877j
[33]	Li, G. W.; Xiao, J.; Zhang, W. Q. Green Chem. 2012, 14, 2234. doi: 10.1039/c2gc35483g
[34]	Xu, G.; Jin, M. C.; Kalkhajeh, Y. K.; Wang, L.; Tao, M. L.; Zhang, W. Q. J. Cleaner Prod. 2019, 231, 77. doi: 10.1016/j.jclepro.2019.05.211
[35]	Hu, Q. Q.; Shi, X. L.; Chen, Y. J.; Han, X. F.; Duan, P. G.; Zhang, W. Q. J. Ind. Eng. Chem. 2017, 54, 75. doi: 10.1016/j.jiec.2017.05.020
[36]	Li, P. Y.; Liu, Y. Y.; Ma, N.; Zhang, W. Q. Catal. Lett. 2018, 148, 813. doi: 10.1007/s10562-017-2287-y
[37]	Li, P. Y.; Mi, L. W.; Liu, Y. Y.; Zhang, W. Q.; Shi, X. L. J. Ind. Eng. Chem. 2020, 81, 323. doi: 10.1016/j.jiec.2019.09.021
[38]	Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. 1985, 24, 1.
[39]	Liu, B. Y.; Zhao, D. S.; Xu, D. Q.; Xu, Z. Y. Chem. Res. Chin. Univ. 2007, 23, 549. doi: 10.1016/S1005-9040(07)60120-2
[40]	Xiao, J.; Li, G. W.; Zhang, W. Q. Chem. Res. Chin. Univ. 2013, 29, 256. doi: 10.1007/s40242-013-2236-2
[41]	Zhu, H.; Zhang, C. L.; Ma, N.; Tao, M. L.; Zhang, W. Q. Appl. Catal., A 2020, 608, 117842. doi: 10.1016/j.apcata.2020.117842
[42]	Wang, L.; Xu, G.; Xiao, J.; Tao, M. L.; Zhang, W. Q. Ind. Eng. Chem. Res. 2019, 58, 12401. doi: 10.1021/acs.iecr.9b01375
[43]	Li, P. Y.; Liu, Y. Y.; Wang, L.; Tao, M. L.; Zhang, W. Q. J. Appl. Polym. Sci. 2018, 135, 45992. doi: 10.1002/app.45992
[44]	Zhang, Z.; Wang, M.; Zhang, C. F.; Zhang, Z. X.; Lu, J. M.; Wang, F. Chem. Commun. 2015, 51, 9205. doi: 10.1039/C5CC02785C
[45]	Zhou, J. G.; Fang, J. J. Org. Chem. 2011, 76, 7730. doi: 10.1021/jo201054k
[46]	Modi, A.; Ali, W.; Mohanta, P. R.; Khatun, N.; Patel, B. K. ACS Sustainable Chem. Eng. 2015, 3, 2582. doi: 10.1021/acssuschemeng.5b00817
[47]	Laha, J. K.; Patel, K. V.; Tummalapalli, K. S.; Dayal, N. Chem. Commun. 2016, 52, 10245. doi: 10.1039/C6CC04259G
[48]	De Vries, J. G. Can. J. Chem. 2001, 79, 1086. doi: 10.1139/v01-033
[49]	Madasu, S. B.; Vekariya, N. A.; Kiran, M. H.; Gupta, B.; Islam, A.; Douglas, P. S.; Babu, K. R. Beilstein J. Org. Chem. 2012, 8, 1400. pmid: 23019477
[50]	Biffis, A.; Centomo, P.; Del Zotto, A.; Zecca, M. Chem. Rev. 2018, 118, 2249. doi: 10.1021/acs.chemrev.7b00443
[51]	Jagtap, S. Catalysts 2017, 7, 267. doi: 10.3390/catal7090267
[52]	Mpungose, P. P.; Vundla, Z. P.; Maguire, G. E.; Friedrich, H. B. Molecules 2018, 23, 1676. doi: 10.3390/molecules23071676
[53]	Xiao, J.; Wang, L.; Zhang, H. N.; Ma, N.; Tao, M. L.; Zhang, W. Q. Chem. Eng. Sci. 2022, 247, 117053. doi: 10.1016/j.ces.2021.117053
[54]	Xiao, J.; Zhang, H. N.; Ejike, A. C.; Wang, L.; Tao, M. L.; Zhang, W. Q. React. Funct. Polym. 2021, 161, 104843. doi: 10.1016/j.reactfunctpolym.2021.104843
[55]	Sruthi, P. R.; Anjali, S.; Varghese, N.; Anas, S. J. Organomet. Chem. 2020, 921, 121354. doi: 10.1016/j.jorganchem.2020.121354
[56]	Sruthi, P. R.; Sarika, V.; Suku, A.; Krishnan, A.; Anas, S. Inorg. Chim. Acta 2020, 502, 119305. doi: 10.1016/j.ica.2019.119305
[57]	Xing, G. Y. Fibers Polym. 2016, 17, 194. doi: 10.1007/s12221-016-4778-7
[58]	Shao, L. J.; Liu., J.; Ye, Y. H.; Zhang, X. M.; Qi, C. Z. Appl. Organomet. Chem. 2011, 25, 699.
[59]	Shao, L. J.; Qi, C. Z. Appl. Catal., A 2013, 468, 26. doi: 10.1016/j.apcata.2013.08.010
[60]	Shao, L. J.; Qi, C. Z. Fibers Polym. 2014, 15, 2233. doi: 10.1007/s12221-014-2233-1
[61]	Guo, L. P.; Bai, J.; Wang, J. Z.; Liang, H. O.; Li, C. P.; Sun, W. Y.; Meng, Q. R. J. Mol. Catal. A: Chem. 2015, 400, 95. doi: 10.1016/j.molcata.2015.02.009
[62]	Han, F. S. Chem. Soc. Rev. 2013, 42, 5270. doi: 10.1039/c3cs35521g
[63]	Zhong, L.; Chokkalingam, A.; Cha, W. S.; Lakhi, K. S.; Su, X. Y.; Lawrence, G.; Vinu, A. Catal. Today 2015, 243, 195. doi: 10.1016/j.cattod.2014.08.038
[64]	Kundu, D.; Patra, A. K.; Sakamoto, J.; Uyama, H. React. Funct. Polym. 2014, 79, 8. doi: 10.1016/j.reactfunctpolym.2014.03.002
[65]	Marziale, A. N.; Jantke, D.; Faul, S. H.; Reiner, T.; Herdtweck, E.; Eppinger, J. Green Chem. 2011, 13, 169. doi: 10.1039/C0GC00522C
[66]	Yu, D. D.; Bai, J.; Wang, J. Z.; Li, C. P. J. Inorg. Organomet. Polym. Mater. 2016, 26, 914. doi: 10.1007/s10904-016-0384-9
[67]	Peshkov, V. A.; Pereshivko, O. P.; Van der Eycken, E. V. Chem. Soc. Rev. 2012, 41, 3790. doi: 10.1039/c2cs15356d
[68]	Huo, X.; Liu, J.; Wang, B. D.; Zhang, H. L.; Yang, Z. Y.; She, X. G.; Xi, P. X. J. Mater. Chem. A 2013, 1, 651. doi: 10.1039/C2TA00485B
[69]	Hashmi, A. S. K. Pure Appl. Chem. 2010, 82, 657. doi: 10.1351/PAC-CON-09-10-17
[70]	Jaimes, M. C. B.; Rominger, F.; Pereira, M. M.; Carrilho, R. M. B.; Carabineiro, S. A. C.; Hashmi, A. S. K. Chem. Commun. 2014, 50, 4937. doi: 10.1039/c4cc00839a
[71]	Cao, J.; Xu, G.; Li, P. Y.; Tao, M. L.; Zhang, W. Q. ACS Sustainable Chem. Eng. 2017, 5, 3438. doi: 10.1021/acssuschemeng.7b00103
[72]	Cao, J.; Li, P. Y.; Xu, G.; Tao, M. L.; Ma, N.; Zhang, W. Q. Chem. Eng. J. 2018, 349, 456. doi: 10.1016/j.cej.2018.05.046
[73]	Hu, Q. Q.; Shi, X. L.; Chen, Y. J.; Wang, F.; Weng, Y. J.; Duan, P. G. J. Ind. Eng. Chem. 2019, 69, 387. doi: 10.1016/j.jiec.2018.09.047
[74]	Shi, X. L.; Sun, B. Y.; Chen, Y. J.; Hu, Q. Q.; Li, P. Y.; Meng, Y. L.; Duan, P. G. J. Catal. 2019, 372, 321. doi: 10.1016/j.jcat.2019.03.020
[75]	Trost, B. M.; Masters, J. T. Chem. Soc. Rev. 2016, 45, 2212. doi: 10.1039/C5CS00892A
[76]	Zhang, B.; Wang, Y.; Yang, S. P.; Zhou, Y.; Wu, W. B.; Tang, W.; Zuo, J. P.; Li, Y.; Yue, J. M. J. Am. Chem. Soc. 2012, 134, 20605. doi: 10.1021/ja310482z pmid: 23214963
[77]	Gholami, M.; Tykwinski, R. R. Chem. Rev. 2006, 106, 4997. doi: 10.1021/cr0505573
[78]	Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. J. Am. Chem. Soc. 2005, 127, 2666. pmid: 15725024
[79]	Shi, X. L.; Hu, Q. Q.; Wang, F.; Zhang, W. Q.; Duan, P. G. J. Catal. 2016, 337, 233. doi: 10.1016/j.jcat.2016.01.022
[80]	Zhang, C. L.; Zhu, H.; Gang, K. Y.; Tao, M. L.; Ma, N.; Zhang, W. Q. React. Funct. Polym. 2021, 160, 104831. doi: 10.1016/j.reactfunctpolym.2021.104831
[81]	Cao, J.; Tian, H. Q. Chem.-Asian J. 2018, 13, 1561. doi: 10.1002/asia.v13.12
[82]	Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. doi: 10.1016/S0022-328X(02)01158-0
[83]	Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem., Int. Ed. 2001, 113, 623. doi: 10.1002/(ISSN)1521-3757
[84]	Toyota, M.; Komori, C.; Ihara, M. J. Org. Chem. 2000, 65, 7110. pmid: 11031036
[85]	Li, J. Z.; Ambroise, A.; Yang, S. I.; Diers, J. R.; Seth, J.; Wack, C. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Am. Chem. Soc. 1999, 121, 8927. doi: 10.1021/ja991730d
[86]	Strachan, J. P.; Gentemann, S.; Seth, J.; Kalsbeck, W. A.; Lindsey, J. S.; Holten, D.; Bocian, D. F. Inorg. Chem. 1998, 37, 1191. doi: 10.1021/ic970967c
[87]	Wang, W. S.; Shangguan, S. H.; Qiu, N.; Hu, C. Q.; Zhang, L.; Hu, Y. Z. Bioorg. Med. Chem. 2013, 21, 2879. doi: 10.1016/j.bmc.2013.03.061
[88]	Fu, T. L.; Wang, I. J. Dyes Pigm. 2008, 76, 590. doi: 10.1016/j.dyepig.2007.02.007
[89]	Puterová, Z.; Romiszewski, J.; Mieczkowski, J.; Gorecka, E. Tetrahedron 2012, 68, 8172. doi: 10.1016/j.tet.2012.07.075
[90]	Narlawar, R.; Lane, J. R.; Doddareddy, M.; Lin, J.; Brussee, J.; IJzerman, A. P. J. Med. Chem. 2010, 53, 3028. doi: 10.1021/jm901252a
[91]	Li, P. Y.; Du, J. G.; Xie, Y. J.; Tao, M. L.; Zhang, W. Q. ACS Sustainable Chem. Eng. 2016, 4, 1139. doi: 10.1021/acssuschemeng.5b01216
[92]	Du, J. G.; Shuai, B.; Tao, M. L.; Wang, G. W.; Zhang, W. Q. Green Chem. 2016, 18, 2625. doi: 10.1039/C5GC02622A
[93]	Yuan, X. Y.; Du, H. M.; Zhao, J. Y.; Chima, A. E.; Ma, N.; Tao, M. L.; Zhang, W. Q. Catal. Lett. 2021, 151, 832. doi: 10.1007/s10562-020-03340-7
[94]	Song, Q. W.; Zhou, Z. H.; He, L. N. Green Chem. 2017, 19, 3707. doi: 10.1039/C7GC00199A
[95]	Lang, X. D.; He, L. N. Chem. Rec. 2016, 16, 1337. doi: 10.1002/tcr.201500293
[96]	Shi, X. L.; Chen, Y. J.; Duan, P. G.; Zhang, W. Q.; Hu, Q. Q. ACS Sustainable Chem. Eng. 2018, 6, 7119. doi: 10.1021/acssuschemeng.8b01051
[97]	Geng, H.; Zhang, C. L.; Tao, M. L.; Ma, N.; Zhang, W. Q. J. CO₂ Util. 2021, 49, 101559.
[98]	Li, P. Y.; Liu, Y. Y.; Mi, L. W.; Shi, X. L.; Duan, P. G.; Cao, J. L.; Zhang, W. Q. Catal. Today 2020, 355, 162. doi: 10.1016/j.cattod.2019.06.049
[99]	Shi, X. L.; Chen, Y. J.; Hu, Q. Q.; Zhang, W. Q.; Luo, C. X.; Duan, P. G. J. Ind. Eng. Chem. 2017, 53, 134.
[100]	Liu, H.; Bai, J.; Wang, S.; Li, C. P.; Guo, L. P.; Liang, H. O.; Xu, T.; Sun, W. Y.; Li, H. Q. Colloids Surf., A 2014, 448, 154. doi: 10.1016/j.colsurfa.2014.02.024
[101]	Du, J. G.; Xu, G.; Lin, H.; Wang, G. W.; Tao, M. L.; Zhang, W. Q. Green Chem. 2016, 18, 2726. doi: 10.1039/C5GC02621K
[102]	Arslan, O.; Eren, H.; Biyikli, N.; Uyar, T. ChemistrySelect 2017, 2, 8790. doi: 10.1002/slct.201701329
[103]	Wang, M. L.; Jiang, T. T.; Lu, Y.; Liu, H. J.; Chen, Y. J. Mater. Chem. A 2013, 1, 5923. doi: 10.1039/c3ta10293a
[104]	Xiao, J.; Wu, Z. Y.; Li, K. L.; Zhao, Z. B.; Liu, C. Y. RSC Adv. 2022, 12, 1051. doi: 10.1039/D1RA07321D
[105]	Shi, X. L.; Chen, Y. J.; Hu, Q. Q.; Wang, F.; Duan, P. G. J. Ind. Eng. Chem. 2018, 60, 333. doi: 10.1016/j.jiec.2017.11.019
[106]	Zhen, Y. Z.; Lin, H. K.; Wang, S. Y.; Tao, M. L. RSC Adv. 2014, 4, 26122. doi: 10.1039/C4RA03985H
[107]	Li, P. Y.; Yang, Y.; Mi, L. W.; Gao, K.; Tao, M. L.; Chen, W. H. Catal. Lett. 2021, 151, 2056. doi: 10.1007/s10562-020-03443-1
[108]	Xie, Y. J.; Liu, X. X.; Tao, M. L. J. Chem. Educ. 2016, 93, 2074. doi: 10.1021/acs.jchemed.5b00933
[109]	Shi, X. L.; Lin, H. K.; Li, P. Y.; Zhang, W. Q. ChemCatChem 2014, 6, 2947. doi: 10.1002/cctc.v6.10
[110]	Xiao, J.; Wang, L.; Ran, J. R.; Zhao, J. Y.; Ma, N.; Tao, M. L.; Zhang, W. Q. J. Cleaner Prod. 2020, 274, 122473. doi: 10.1016/j.jclepro.2020.122473
[111]	Xu, G.; Cao, J.; Zhao, Y. L.; Zheng, L. S.; Tao, M. L.; Zhang, W. Q. Chem.-Asian J. 2017, 12, 2565. doi: 10.1002/asia.v12.19
[112]	Li, P. Y.; Liu, Y. Y.; Cao, J.; Tao, M. L.; Zhang, W. Q. ChemCatChem 2017, 9, 3725. doi: 10.1002/cctc.201700515
[113]	Shi, X. L.; Sun, B. Y.; Hu, Q. Q.; Liu, K.; Li, P. Y.; Liu, B. Z. Chem. Eng. J. 2020, 395, 125084. doi: 10.1016/j.cej.2020.125084
[114]	Shi, X. L.; Sun, B. Y.; Hu, Q. Q.; Chen, Y. J.; Duan, P. G. Green Chem. 2019, 21, 3573. doi: 10.1039/C9GC00987F
[115]	Wu, J.; Du, X. L.; Ma, J.; Zhang, Y. P.; Shi, Q. C.; Luo, L. J.; Song, B. A.; Yang, S.; Hu, D. Y. Green Chem. 2014, 16, 3210. doi: 10.1039/C3GC42400F
[116]	Chen, J. X.; Su, W. K.; Wu, H. Y.; Liu, M. C.; Jin, C. Green Chem. 2007, 9, 972. doi: 10.1039/b700957g
[117]	Wu, Z. C.; Wu, Q.; Chen, M.; Tao, T. X. Asian J. Chem. 2013, 25, 5783. doi: 10.14233/ajchem
[118]	Bergbreiter, D. E.; Osburn, P. L.; Frels, J. D. J. Am. Chem. Soc. 2001, 123, 5783.
[119]	Hwang, Y. K.; Hong, D. Y.; Chang, J. S.; Jhung, S. H.; Seo, Y. K.; Kim, J.; Vimont, A.; Daturi, M.; Serre, C.; Férey, G. Angew. Chem., Int. Ed. 2008, 120, 4212. doi: 10.1002/(ISSN)1521-3757
[120]	Tabatabaei Rezaei, S. J.; Shamseddin, A.; Ramazani, A.; Mashhadi Malekzadeh, A.; Azimzadeh Asiabi, P. Appl. Organomet. Chem. 2017, 31, e3707.
[121]	Kaneko, T.; Tanaka, S.; Asao, N.; Yamamoto, Y.; Chen, M. W.; Zhang, W.; Inoue, A. Adv. Synth. Catal. 2011, 353, 2927. doi: 10.1002/adsc.v353.16
[122]	Modak, A.; Mondal, J.; Sasidharan, M.; Bhaumik, A. Green Chem. 2011, 13, 1317. doi: 10.1039/c1gc15045f
[123]	Ju, P. Y.; Wu, S. J.; Su, Q.; Li, X. D.; Liu, Z. Q.; Li, G. H.; Wu, Q. L. J. Mater. Chem. 2019, 7, 2660.
[124]	Zhan, K.; You, H. H.; Liu, W. Y.; Lu, J.; Lu, P.; Dong, J. React. Funct. Polym. 2011, 71, 756. doi: 10.1016/j.reactfunctpolym.2011.04.007
[125]	Liu, P.; Li, P. H.; Wang, L. Synth. Commun. 2012, 42, 2595. doi: 10.1080/00397911.2011.563024
[126]	Islam, S. M.; Salam, N.; Mondal, P.; Roy, A. S.; Ghosh, K.; Tuhina, K. J. Mol. Catal. 2014, 387, 7. doi: 10.1016/j.molcata.2014.02.007
[127]	Altman, R. A.; Koval, E. D.; Buchwald, S. L. J. Org. Chem. 2007, 72, 6190. pmid: 17625886
[128]	Devarajan, N.; Suresh, P. ChemCatChem 2016, 8, 2953. doi: 10.1002/cctc.201600480
[129]	Anbu, N.; Dhakshinamoorthy, A. J. Ind. Eng. 2018, 65, 120.
[130]	Dutta, M. M.; Phukan, P. Catal. Commun. 2018, 109, 38. doi: 10.1016/j.catcom.2018.02.014
[131]	Muñoz, A.; Leo, P.; Orcajo, G.; Martínez, F.; Calleja, G. ChemCatChem 2019, 11, 3376. doi: 10.1002/cctc.v11.15
[132]	Borah, R. K.; Raul, P. K.; Mahanta, A.; Shchukarev, A.; Mikkola, J. P.; Thakur, A. J. Synlett 2017, 28, 1177. doi: 10.1055/s-0036-1588741