Abstract
Increasing the efficiency of cross-coupling reaction under mild condition and easy catalyst separation is a key issue in the realistically chemical industry application. Here, we report that the fiber-supported Pd catalyst shows a high activity and selectivity for the cross-coupling reaction of terminal alkynes. The yield of the asymmetric 1,3-diyne can reach 83% at 80 °C and 4 h reaction time in N,N-dimethylacetamide (DMAc), and about 87% selectivity. XPS, EDS and SEM results show that Pd metal ions are successfully loaded onto the fiber surface and are reduced to produce active component of Pd (0) by terminal alkyne in reaction. We consider that Pd (0) is the active center of the catalytic cycle, the coordination of the fibers can stabilize Pd particles on the supports and increases the catalytic activity of Pd catalysts. Cu (I) plays a synergistic catalytic role. This study provides an alternative pathway for the high efficient cross-coupling reaction.
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References
Roşca DA, Radkowski K, Wolf LM, Wagh M, Goddard R, Thiel W, Fürstner A (2017) J Am Chem Soc 139:2443
Sindhu KS, Anilkumar G (2014) RSC Adv 4:27867
Zhou G, Zhao XM, Dan WY (2017) Tetrahedron Lett 58:3085
Wu WQ, Jiang HF (2014) Acc Chem Res 47:2483
Alonso F, Yus M (2012) ACS Catal 2:1441
Batsanov AS, Collings JC, Fairlamb IJ, Holland JP, Howard JA, Lin ZY, Marder TB, Parsons AC, Ward RM, Zhu J (2005) J Org Chem 70:703
Meng X, Li CB, Han BC, Wang TS, Chen BH (2010) Tetrahedron 66:4029
Navale BS, Bhat RG (2013) RSC Adv 3:5220
Zhang SL, Liu XY, Wang TQ (2011) Adv Synth Catal 353:1463
Ma ZY, Wang XY, Wei SY, Yang HL, Zhang FW, Wang P, Xie M, Ma JT (2013) Catal Commun 39:24
Biswas S, Mullick K, Chen SY, Kriz DA, Shakil MD, Kuo CH, Angeles-Boza AM, Rossi AR, Suib SL (2016) ACS Catal 6:5069
Lai BB, Bai RX, Gu YL (2018) ACS Sustain Chem Eng 6:17076
Xu ZT, Ai JT, Cai MZ (2018) J Chem Res 42:133
Yu L, Huang YP, Wei Z, Ding YH, Su CL, Xu Q (2015) J Org Chem 80:8677
Zhang DL, Wei Z, Yu L (2017) Sci Bull 62:1325
Yu L, Han Z, Ding YH (2016) Org Process Res Dev 20:2124
Wang Q, Jing XB, Han J, Yu L, Xu Q (2018) Mater Lett 215:65
Liu YH, Tang DL, Cao KH, Yu L, Han J, Xu Q (2018) J Catal 360:250
Wu ZC, Yang Q, Ge X, Ren YM, Yang RC, Tao TX (2017) Catal Lett 147:1333
Djakovitch L, Koehler K (1999) J Mol Catal A 142:275
Siemsen P, Livingston RC, Diederich F (2010) Angew Chem Int Edit 39:2632
Shi W, Luo YD, Luo XC, Chao L, Zhang H, Wang J, Lei AW (2008) J Am Chem Soc 130:14713
Wang YL, Suo QL, Han LM, Guo LL, Wang YQ, Li FW (2018) Tetrahedron 74:1918
Mohanty A, Roy S (2017) Chem Commun 53:10796
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This research was sponsored by the National Natural Science Foundation of China (Grant Nos. 21571003, 51572004).
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Li, H., Chen, X., Tao, T. et al. Fiber-supported Pd Catalysts for Cross-coupling Reaction of Aromatic and Aliphatic Terminal Alkynes. Catal Lett 149, 2390–2396 (2019). https://doi.org/10.1007/s10562-019-02820-9
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DOI: https://doi.org/10.1007/s10562-019-02820-9