Phenylboronic acid functionalized polyacrylonitrile fiber for efficient and green synthesis of bis(indolyl)methane derivatives

doi:10.1016/j.cjche.2021.08.029

Abstract

Abstract: The use of fiber as a catalyst carrier to construct heterogeneous catalysts with good catalytic activity and recycling performance has received wide attention. In this study, three phenylboronic acid functionalized polyacrylonitrile fiber (PANF) catalysts were synthesized by amination and quaternization. Fourier transform infrared spectroscopy, X-ray diffractometry, scanning electron microscopy, and X-ray photoelectron spectroscopy were used to verify the successful grafting of phenylboronic acid and the structural integrity of the fiber catalyst after recycling. The activity of the catalysts was explored with the Friedel–Crafts alkylation between indole and aromatic aldehydes. The results indicate that the synthesized catalyst (PAN_p-BAF) in which the phenylboronic acid functional group was linked at the para position, exhibited the highest catalytic activity for the Friedel–Crafts alkylation. The substrate scope experiments confirmed that the catalyst has outstanding catalytic activity for most aromatic aldehydes, especially for those containing moderate electron donating groups. Moreover, the catalyst can be reused eight times in water without significant decrease in its catalytic activity. Further, the scale-up experiment confirmed that the fiber catalyst has a certain potential for industrial application.

Key words: Polymers, Phenylboronic acid, Catalyst support, Friedel–Crafts alkylation, Sustainability

摘要： The use of fiber as a catalyst carrier to construct heterogeneous catalysts with good catalytic activity and recycling performance has received wide attention. In this study, three phenylboronic acid functionalized polyacrylonitrile fiber (PANF) catalysts were synthesized by amination and quaternization. Fourier transform infrared spectroscopy, X-ray diffractometry, scanning electron microscopy, and X-ray photoelectron spectroscopy were used to verify the successful grafting of phenylboronic acid and the structural integrity of the fiber catalyst after recycling. The activity of the catalysts was explored with the Friedel–Crafts alkylation between indole and aromatic aldehydes. The results indicate that the synthesized catalyst (PAN_p-BAF) in which the phenylboronic acid functional group was linked at the para position, exhibited the highest catalytic activity for the Friedel–Crafts alkylation. The substrate scope experiments confirmed that the catalyst has outstanding catalytic activity for most aromatic aldehydes, especially for those containing moderate electron donating groups. Moreover, the catalyst can be reused eight times in water without significant decrease in its catalytic activity. Further, the scale-up experiment confirmed that the fiber catalyst has a certain potential for industrial application.

关键词: Polymers, Phenylboronic acid, Catalyst support, Friedel–Crafts alkylation, Sustainability

Haonan Zhang, Haotian Zhang, Minli Tao, Wenqin Zhang. Phenylboronic acid functionalized polyacrylonitrile fiber for efficient and green synthesis of bis(indolyl)methane derivatives[J]. Chinese Journal of Chemical Engineering, 2022, 51(11): 1-9.

References

[1] T.R. Garbe, M. Kobayashi, N. Shimizu, N. Takesue, M. Ozawa, H. Yukawa, Indolyl carboxylic acids by condensation of indoles with α-keto acids, J. Nat. Prod. 63 (5) (2000) 596-598
[2] K.V. Sashidhara, A. Kumar, M. Kumar, A. Srivastava, A.J. Puri, Synthesis and antihyperlipidemic activity of novel coumarin bisindole derivatives, Bioorg. Med. Chem. Lett. 20 (22) (2010) 6504-6507
[3] C.B. Hong, G.L. Firestone, L.F. Bjeldanes, Bcl-2 family-mediated apoptotic effects of 3, 3'-diindolylmethane (DIM) in human breast cancer cells, Biochem. Pharmacol. 63 (6) (2002) 1085-1097
[4] X.K. Ge, S. Yannai, G. Rennert, N. Gruener, F.A. Fares, 3, 3'-diindolylmethane induces apoptosis in human cancer cells, Biochem. Biophys. Res. Commun. 228 (1) (1996) 153-158
[5] S.B. Bharate, J.B. Bharate, S.I. Khan, B.L. Tekwani, M.R. Jacob, R. Mudududdla, R.R. Yadav, B. Singh, P.R. Sharma, S. Maity, B. Singh, I.A. Khan, R.A. Vishwakarma, Discovery of 3, 3'-diindolylmethanes as potent antileishmanial agents, Eur. J. Med. Chem. 63 (2013) 435-443
[6] F. Shirini, M.P. Lati, BiVO₄-NPs:An efficient nano-catalyst for the synthesis of biscoumarins, bis(indolyl)methanes and 3, 4-dihydropyrimidin-2(1H)-ones (thiones) derivatives, J. Iran. Chem. Soc. 14 (1) (2017) 75-87
[7] D. Li, J. Wang, F. Chen, H. Jing, Fe₃O₄@SiO₂ supported aza-crown ether complex cation ionic liquids:Preparation and applications in organic reactions, RSC Adv. 7 (2017) 4237-4242
[8] B.R. Nemallapudi, G.V. Zyryanov, B. Avula, M.R. Guda, S.R. Cirandur, C. Venkataramaiah, W. Rajendra, S. Gundala, Meglumine as a green, efficient and reusable catalyst for synthesis and molecular docking studies of bis(indolyl)methanes as antioxidant agents, Bioorg. Chem. 87 (2019) 465-473
[9] S.A. Sadaphal, K.F. Shelke, S.S. Sonar, M.S. Shingare, Ionic liquid promoted synthesis of bis(indolyl) methanes, Cent. Eur. J. Chem. 6 (4) (2008) 622-626
[10] D.Q. Liang, W.Z. Huang, L. Yuan, Y.H. Ma, J.M. Ma, D.M. Ning, An underrated cheap Lewis acid:Molecular bromine as a robust catalyst for bis(indolyl)methanes synthesis, Catal. Commun. 55 (2014) 11-14
[11] S.J. Ji, S.Y. Wang, Y. Zhang, T.P. Loh, Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions, Tetrahedron 60 (9) (2004) 2051-2055
[12] Y.J. Fu, Z.P. Lu, K. Fang, X.Y. He, H.J. Xu, Y. Hu, Enzymatic approach to cascade synthesis of bis(indolyl)methanes in pure water, RSC Adv. 10 (18) (2020) 10848-10853
[13] E. Fernández, A. Whiting, Synthesis and Application of Organoboron Compounds, Springer, Cham, Switzerland, 2015
[14] A. Coca, Boron reagents in synthesis, ACS Symp. Ser. 1236 (2016) 1-523
[15] R.M. Al-Zoubi, O. Marion, D.G. Hall, Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature, Angew. Chem. Int. Ed. 47 (15) (2008) 2876-2879
[16] H.C. Zheng, D.G. Hall, Mild and efficient boronic acid catalysis of Diels-Alder cycloadditions to 2-alkynoic acids, Tetrahedron Lett. 51 (27) (2010) 3561-3564
[17] T. Azuma, A. Murata, Y. Kobayashi, T. Inokuma, Y. Takemoto, A dual arylboronic acid-aminothiourea catalytic system for the asymmetric intramolecular hetero-Michael reaction of α, β-unsaturated carboxylic acids, Org. Lett. 16 (16) (2014) 4256-4259
[18] N. Gernigon, R.M. Al-Zoubi, D.G. Hall, Direct amidation of carboxylic acids catalyzed by ortho-iodo arylboronic acids:Catalyst optimization, scope, and preliminary mechanistic study supporting a peculiar halogen acceleration effect, J. Org. Chem. 77 (19) (2012) 8386-8400
[19] T. Maki, K. Ishihara, H. Yamamoto, N-alkyl-4-boronopyridinium salts as thermally stable and reusable amide condensation catalysts, Org. Lett. 7 (22) (2005) 5043-5046
[20] K. Ishihara, S. Kondo, H. Yamamoto, 3, 5-bis(perfluorodecyl)phenylboronic acid as an easily recyclable direct amide condensation catalyst, Synlett 2001 (9) (2001) 1371-1374
[21] T. Maki, K. Ishihara, H. Yamamoto, New boron(III)-catalyzed amide and ester condensation reactions, Tetrahedron 63 (35) (2007) 8645-8657
[22] T. Maki, K. Ishihara, H. Yamamoto, N-alkyl-4-boronopyridinium halides versus boric acid as catalysts for the esterification of α-hydroxycarboxylic acids, Org. Lett. 7 (22) (2005) 5047-5050
[23] Y.J. Cao, Y.Y. Lai, X. Wang, Y.J. Li, W.J. Xiao, Michael additions in water of ketones to nitroolefins catalyzed by readily tunable and bifunctional pyrrolidine-thiourea organocatalysts, Tetrahedron Lett. 48 (1) (2007) 21-24
[24] A.R. Horrocks, B.K. Kandola, P.J. Davies, S. Zhang, S.A. Padbury, Developments in flame retardant textiles -A review, Polym. Degrad. Stab. 88 (1) (2005) 3-12
[25] M. Yu, Z.Q. Wang, H.Z. Liu, S.Y. Xie, J.X. Wu, H.Q. Jiang, J.Y. Zhang, L.F. Li, J.Y. Li, Laundering durability of photocatalyzed self-cleaning cotton fabric with TiO₂ nanoparticles covalently immobilized, ACS Appl. Mater. Interfaces 5 (9) (2013) 3697-3703
[26] Y. Shin, D.I. Yoo, K. Son, Development of thermoregulating textile materials with microencapsulated phase change materials (PCM). II. Preparation and application of PCM microcapsules, J. Appl. Polym. Sci. 96 (6) (2005) 2005-2010
[27] J. Cao, P.Y. Li, G. Xu, M.L. Tao, N. Ma, W.Q. Zhang, Cooperative N-heterocyclic carbene Au and amino catalysis for continuous synthesis of secondary propargylamines in a fiber supported hydrophilic microenvironment, Chem. Eng. J. 349 (2018) 456-465
[28] J. Xiao, G. Xu, L. Wang, P.Y. Li, W.Q. Zhang, N. Ma, M.L. Tao, Polyacrylonitrile fiber with strongly acidic electrostatic microenvironment:Highly efficient and recyclable heterogeneous catalyst for the synthesis of heterocyclic compounds, J. Ind. Eng. Chem. 77 (2019) 65-75
[29] H. Zhu, G. Xu, H.M. Du, C.L. Zhang, N. Ma, W.Q. Zhang, Prolinamide functionalized polyacrylonitrile fiber with tunable linker length and surface microenvironment as efficient catalyst for Knoevenagel condensation and related multicomponent tandem reactions, J. Catal. 374 (2019) 217-229
[30] P.Y. Li, Y.Y. Liu, N. Ma, W.Q. Zhang, L-lysine functionalized polyacrylonitrile fiber:A green and efficient catalyst for Knoevenagel condensation in water, Catal. Lett. 148 (3) (2018) 813-823
[31] P.Y. Li, J.G. Du, Y.J. Xie, M.L. Tao, W.Q. Zhang, Highly efficient polyacrylonitrile fiber catalysts functionalized by aminopyridines for the synthesis of 3-substituted 2-aminothiophenes in water, ACS Sustainable Chem. Eng. 4 (3) (2016) 1139-1147
[32] J.G. Du, G. Xu, H.K. Lin, G.W. Wang, M.L. Tao, W.Q. Zhang, Highly efficient reduction of carbonyls, azides, and benzyl halides by NaBH₄ in water catalyzed by PANF-immobilized quaternary ammonium salts, Green Chem. 18 (9) (2016) 2726-2735
[33] G. Xu, L. Wang, M.M. Li, M.L. Tao, W.Q. Zhang, Phosphorous acid functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment for one-pot C-C and C-N bond formation reactions, Green Chem. 19 (24) (2017) 5818-5830
[34] W.S. Xu, W.J. Zheng, F.J. Wang, Q.Z. Xiong, X.L. Shi, Y.K. Kalkhajeh, G. Xu, H.J. Gao, Using iron ion-loaded aminated polyacrylonitrile fiber to efficiently remove wastewater phosphate, Chem. Eng. J. 403 (2021) 126349
[35] N. Piergies, E. Proniewicz, Y. Ozaki, Y. Kim, L.M. Proniewicz, Influence of substituent type and position on the adsorption mechanism of phenylboronic acids:Infrared, Raman, and surface-enhanced Raman spectroscopy studies, J. Phys. Chem. A 117 (27) (2013) 5693-5705
[36] S.P. Rwei, T.F. Way, W.Y. Chiang, S.Y. Pan, Effect of tacticity on the cyclization of polyacrylonitrile copolymers, Colloid Polym. Sci. 295 (5) (2017) 803-815
[37] J. Xiao, H.N. Zhang, A.C. Ejike, L. Wang, M.L. Tao, W.Q. Zhang, Phenanthroline functionalized polyacrylonitrile fiber with Pd(0) nanoparticles as a highly active catalyst for the Heck reaction, React. Funct. Polym. 161 (2021) 104843
[38] K.X. Zhang, C. Qu, Z.B. Liang, S. Gao, H. Zhang, B.J. Zhu, W. Meng, E.G. Fu, R.Q. Zou, Highly dispersed Co-B/N codoped carbon nanospheres on graphene for synergistic effects as bifunctional oxygen electrocatalysts, ACS Appl. Mater. Interfaces 10 (36) (2018) 30460-30469
[39] J.L. Zhu, C.Y. He, Y.Y. Li, S. Kang, P.K. Shen, One-step synthesis of boron and nitrogen-dual-self-doped graphene sheets as non-metal catalysts for oxygen reduction reaction, J. Mater. Chem. A 1 (46) (2013) 14700
[40] H. Tabassum, A. Mahmood, Q. Wang, W. Xia, Z. Liang, B. Qiu, R. Zhao, R. Zou, Hierarchical cobalt hydroxide and B/N Co-doped graphene nanohybrids derived from metal-organic frameworks for high energy density asymmetric supercapacitors, Sci. Rep. 7 (2017) 43084
[41] X.Y. Yuan, H.M. Du, J.Y. Zhao, A.E. Chima, N. Ma, M.L. Tao, W.Q. Zhang, Tuning microenvironment of quaternary ammonium salt and tertiary amine bifunctionalized polyacrylonitrile fiber for cooperatively catalyzed aza-Michael addition, Catal. Lett. 151 (3) (2021) 832-843
[42] P.Y. Li, Y.Y. Liu, L. Wang, M.L. Tao, W.Q. Zhang, Modified polyacrylonitrile fiber as a renewable heterogeneous base catalyst for Henry reaction and Gewald reaction in water, J. Appl. Polym. Sci. 135 (11) (2018) 45992