Abstract
Herein, the multiphase catalyst was prepared for catalytic Suzuki–Miyaura cross-coupling reactions by anchoring palladium nanoparticles on tris(pentaethylene-pentamine)triazine modified boron nitride nanosheets (BNNSs-TPEPTA-Pd). The synthesized catalysts were characterized using various spectroscopic and microscopic techniques such as Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), and transmission electron microscopy (TEM), inductively coupled plasma-optical emission spectroscopy (ICP-OES). Subsequent experiments showed that BNNSs-TPEPTA-Pd is an excellent two-dimensional heterogeneous catalyst with a wide range of substrate tolerance, achieving an excellent yield of 95% within 45 min. On average, the catalyst improved the biaryl yield by about 12% and reduzced the reaction time by 4.6 h. In addition, the catalytic effect remained high after eight catalytic cycles.
Graphical Abstract
An efficient, stable, and recyclable heterogeneous catalyst was prepared by anchoring palladium nanoparticles on tris(pentaethylene-pentamine)triazine modified boron nitride nanosheets (BNNSs-TPEPTA-Pd). The catalyst was used in the Suzuki–Miyaura cross-coupling reaction to verify its activity.
Similar content being viewed by others
References
Lloyd-Williams P, Giralt E (2001) Chem Soc Rev 30(3):145–157
Stanforth SP (1998) Tetrahedron 54(3):263–303
Beletskaya IP, Alonso F, Tyurin V (2019) Coord Chem Rev 385:137–173
Patel KN, Bedekar AV (2015) Catal Lett 145(9):1710–1717
D’Alterio MC, Casals-Cruaas R, Tzouras NV, Talarico G, Nolan SP, Poater A (2021) Chem Eur J 27(54):13481–13493
Stevens PD, Li G, Fan J, Yen M, Gao Y (2005) Chem Commun (Camb) 37(35):4435–4437
Blaser HU, Indolese A, Schnyder A, Steiner H, Studer M (2001) J Mol Catal A Chem 173(1):3–18
Spinella SM, Guan ZH, Chen J, Zhang XM (2009) Synthesis (Stuttg) 2009(18):3094–3098
Chaudhary AR, Bedekar AV (2012) Appl Organomet Chem 26(8):430–437
Sun LJ, Li Q, Zheng M, Lin SY, Guo CL, Luo LY, Guo SE, Li YX, Wang C, Jiang BJ (2021) J Colloid Interface Sci 608(3):2463–2471
Sobhani S, Habibollahi A, Zeraatkar Z (2019) Org Process Res Dev 23(7):1321–1332
Fu Q, Meng Y, Fang Z, Hu Q, Xu L, Gao W, Huang X, Xue Q, Sun YP, Lu F (2017) ACS Appl Mater Interfaces 9(3):2469–2476
Patel HA, Patel AL, Bedekar AV (2015) Appl Organomet Chem 29(1):1–6
Borhade SR, Waghmode SB (2011) Beilstein J Org Chem 7(1):310–319
Augustyniak AW, Zawartka W, Navarro JA, Trzeciak AM (2016) Dalton Trans 45(34):13525–13531
Qian Y, Jung SY, Jin MJ (2019) Bull Korean Chem Soc 40(6):477–478
Hong K, Sajjadi M, Suh JM, Zhang K, Nasrollahzadeh M, Jang HW, Varma RS, Shokouhimehr M (2020) ACS Appl Nano Mater 3(3):2070–2103
Meyer N, Bekaert K, Pirson D, Devillers M, Hermans S (2012) Catal Commun 29:170–174
Postole G, Caldararu M, Ionescu NI, Bonnetot B, Auroux A, Guimon C (2005) Thermochim Acta 434(1–2):150–157
Kong D, Zhang D, Guo H, Zhao J, Wang Z, Hu H, Xu J, Fu C (2019) Polymers (Basel) 11(3):440
Wang J, Zhao D, Zou X, Mao L, Shi L (2017) J Mater Sci Mater Electron 28(17):12984–12994
Li H, Zhao J, Wang J (2021) Compos Sci Technol 201(15):108545
Zhi C, Bando Y, Tang C, Kuwahara H, Golberg D (2009) Adv Mater 21(28):2889–2893
Lin S, Huang J, Ye X (2014) Appl Surf Sci 320:237–243
Zhu H, Zhao X, Li H, Zhao R (2020) Phys Chem Chem Phys 22(7):4023–4031
Farmanzadeh D, Askari Ardehjani N (2018) Appl Surf Sci 444:642–649
Lin Y, Connell JW (2012) Nanoscale 4(22):6908–6939
Nasrollahzadeh M, Bakhshali-Dehkordi R, Kamali TA, Orooji Y, Shokouhimehr M (2021) J Mol Struct 1244:130873
Shafiei N, Nasrollahzadeh M, Baran T, Baran NY, Shokouhimehr M (2021) Carbohydr Polym 262:117920
Ahadi A, Rostamnia S, Panahi P, Wilson LD, Kong Q, An Z, Shokouhimehr M (2019) Catalysts 9(2):140
Choi K-H, Shokouhimehr M, Sung Y-E (2013) Bull Korean Chem Soc 34(5):1477–1480
Golestanzadeh M, Naeimi H (2019) RSC Adv 9(47):27560–27573
Kim K, Kim M, Hwang Y, Kim J (2014) Ceram Int 40(1):2047–2056
Ma X, Lv G, Cheng X, Li W, Sang R, Zhang Y, Wang Q, Hai L, Wu Y (2017) Appl Organomet Chem 31(12):e3854
Wang N, Ma L, Wang J, Zhang Y, Jiang R (2019) ChemPlusChem 84(8):1164–1168
Antony AM, Kandathil V, Kempasiddaiah M, Sasidhar BS, Patil SA, Patil SA (2020) Catal Lett 151(5):1293–1308
Sanaei M, Fazaeli R, Aliyan H (2019) J Chin Chem Soc 66(10):1290–1295
Ohtaka A, Kono Y, Teratani T, Fujii S, Matsuzawa S, Nakamura Y, Nomura R (2011) Catal Lett 141(8):1097–1103
Yu D, Bai J, Wang J, Li C (2016) J Inorg Organomet Polym Mater 26(4):914–920
Dong Y, Wu X, Chen X, Wei Y (2017) Carbohydr Polym 160:106–114
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Zhang, T., Li, G., Zhang, X. et al. Modified Boron Nitride Nanosheets-Loaded Palladium Nanoparticles: An Air-Stable, Highly Active, and Recyclable Multiphase Catalyst for the Suzuki Reaction. Catal Lett 154, 224–236 (2024). https://doi.org/10.1007/s10562-022-04160-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-022-04160-7