Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1241-1270.DOI: 10.6023/cjoc202209003 Previous Articles Next Articles
REVIEWS
收稿日期:
2022-09-03
修回日期:
2022-10-13
发布日期:
2022-11-15
通讯作者:
应安国
基金资助:
Linsheng Bai, Peng Hong, Anguo Ying()
Received:
2022-09-03
Revised:
2022-10-13
Published:
2022-11-15
Contact:
Anguo Ying
Supported by:
Share
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.
Entry | Catalyst | Catalyst amount/mol% | Rection condition | Yielda/% | Reuse time | Ref |
---|---|---|---|---|---|---|
1 | AOFs-Pd(0) | 0.8 | DMF, 110 ℃, 3 h | 95.5 | 3 | [ |
2 | Pd(PNODAM-5) | 2.0 | Heptane, 100 ℃, 22 h | 96 | 3 | [ |
3 | Pd/APS-MIL-101 | 0.93 | DMF, 120 ℃, 1 h | 97 | — | [ |
4 | FeO3O4@PCA/Pd(0)-b-PEG | 0.05 | H2O, 90 ℃, 2 h | 98 | 10 | [ |
5 | PdNPore | 2.0 | MeOH, 80 ℃, 18 h | 94 | 5 | [ |
6 | Pd-MPTAT-1 | 0.97 | H2O/EtOH (V∶V=1∶1), reflux, 6 h | 95 | 2 | [ |
7 | Pd-SP-CMP | 0.6 | 1,4-Dioxane/H2O (V∶V=1∶1), 80 ℃, 12 h | 99 | — | [ |
8 | Pd@IPN | 0.0229 | H2O, 100 ℃, 12 h | 96 | 11 | [ |
9 | PANPhenF-Pd(0) | 0.1 | Solvent-free, 110 ℃, 3 h | 97 | 6 | [ |
Entry | Catalyst | Catalyst amount/mol% | Rection condition | Yielda/% | Reuse time | Ref |
---|---|---|---|---|---|---|
1 | AOFs-Pd(0) | 0.8 | DMF, 110 ℃, 3 h | 95.5 | 3 | [ |
2 | Pd(PNODAM-5) | 2.0 | Heptane, 100 ℃, 22 h | 96 | 3 | [ |
3 | Pd/APS-MIL-101 | 0.93 | DMF, 120 ℃, 1 h | 97 | — | [ |
4 | FeO3O4@PCA/Pd(0)-b-PEG | 0.05 | H2O, 90 ℃, 2 h | 98 | 10 | [ |
5 | PdNPore | 2.0 | MeOH, 80 ℃, 18 h | 94 | 5 | [ |
6 | Pd-MPTAT-1 | 0.97 | H2O/EtOH (V∶V=1∶1), reflux, 6 h | 95 | 2 | [ |
7 | Pd-SP-CMP | 0.6 | 1,4-Dioxane/H2O (V∶V=1∶1), 80 ℃, 12 h | 99 | — | [ |
8 | Pd@IPN | 0.0229 | H2O, 100 ℃, 12 h | 96 | 11 | [ |
9 | PANPhenF-Pd(0) | 0.1 | Solvent-free, 110 ℃, 3 h | 97 | 6 | [ |
Entry | Catalyst | Rection condition | Yielda/% | Reuse time | Ref. |
---|---|---|---|---|---|
1 | SiO2-NHC-Cu | MeOH, 50 ℃, 3 h | 90 | 6 | [ |
2 | Ps-Cu | MeOH, 40 ℃, 10 h | 99 | 5 | [ |
3 | Cu@PI-COF | MeOH-H2O, r.t., 8 h | 87 | 8 | [ |
4 | Cu-(tpa)MOF | EtOH, Et3N, r.t., 12 h | 99 | 5 | [ |
5 | Cu3(BTC)2 | EtOH, Et3N, 60 ℃, 12 h | 92 | 4 | [ |
6 | Cu-doped CoFe2O4 | MeOH, Et3N, r.t., 5 h | 92 | 7 | [ |
7 | URJC-1-MOF | DMF, K2CO3, r.t., 15 h | 61 | 5 | [ |
8 | CuO NPs | MeOH-H2O, r.t., 10 h | 88 | 6 | [ |
9 | CuCl2@PANPA-2F | MeOH, 60 ℃, 3 h | 98 | 5 | [ |
Entry | Catalyst | Rection condition | Yielda/% | Reuse time | Ref. |
---|---|---|---|---|---|
1 | SiO2-NHC-Cu | MeOH, 50 ℃, 3 h | 90 | 6 | [ |
2 | Ps-Cu | MeOH, 40 ℃, 10 h | 99 | 5 | [ |
3 | Cu@PI-COF | MeOH-H2O, r.t., 8 h | 87 | 8 | [ |
4 | Cu-(tpa)MOF | EtOH, Et3N, r.t., 12 h | 99 | 5 | [ |
5 | Cu3(BTC)2 | EtOH, Et3N, 60 ℃, 12 h | 92 | 4 | [ |
6 | Cu-doped CoFe2O4 | MeOH, Et3N, r.t., 5 h | 92 | 7 | [ |
7 | URJC-1-MOF | DMF, K2CO3, r.t., 15 h | 61 | 5 | [ |
8 | CuO NPs | MeOH-H2O, r.t., 10 h | 88 | 6 | [ |
9 | CuCl2@PANPA-2F | MeOH, 60 ℃, 3 h | 98 | 5 | [ |
Entry | Fiber | Retention strength/cN | Retention of breaking strengtha/% |
---|---|---|---|
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 |
Entry | Fiber | Retention strength/cN | Retention of breaking strengtha/% |
---|---|---|---|
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 |
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 |
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 |
[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 |
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