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N-doped carbon supported Pd catalysts for N-formylation of amines with CO2/H2

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Abstract

Using mesoporous N-doped carbons (NCs) derived from glucose and melamine as the supports, a series of Pd/NC catalysts were prepared, in which Pd nanoparticles with average size<2.0 nm were uniformly distributed on the supports. It was indicated that the resultant Pd/NC catalysts were effective for N-formylation of amines with CO2 and H2 in ethanol without any additives. Especially, the catalyst Pd/NC-800-6.9% containing quaternary N showed the best performance, affording a series of formylamides in good or even excellent yields. Further investigation reveals that the interaction between the Pd nanoparticles and quaternary nitrogen in the NC support was responsible for the good performance of the catalyst.

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References

  1. Álvarez A, Bansode A, Urakawa A, Bavykina AV, Wezendonk TA, Makkee M, Gascon J, Kapteijn F. Chem Rev, 2017, 117: 9804–9838

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Zhu Q, Ma J, Kang X, Sun X, Liu H, Hu J, Liu Z, Han B. Angew Chem Int Ed, 2016, 55: 9012–9016

    Article  CAS  Google Scholar 

  3. Li Y, Chan SH, Sun Q. Nanoscale, 2015, 7: 8663–8683

    Article  CAS  PubMed  Google Scholar 

  4. Dong K, Razzaq R, Hu Y, Ding K. Top Curr Chem, 2017, 375: 23

    Article  CAS  Google Scholar 

  5. Sakakura T, Choi JC, Yasuda H. Chem Rev, 2007, 107: 2365–2387

    Article  CAS  PubMed  Google Scholar 

  6. Cui X, Dai X, Zhang Y, Deng Y, Shi F. Chem Sci, 2014, 5: 649–655

    Article  CAS  Google Scholar 

  7. Bobbink FD, Das S, Dyson PJ. Nat Protoc, 2017, 12: 417–428

    Article  CAS  PubMed  Google Scholar 

  8. Daw P, Chakraborty S, Leitus G, Diskin-Posner Y, Ben-David Y, Milstein D. ACS Catal, 2017, 7: 2500–2504

    Article  CAS  Google Scholar 

  9. Liu XF, Li XY, Qiao C, Fu HC, He LN. Angew Chem Int Ed, 2017, 56: 7425–7429

    Article  CAS  Google Scholar 

  10. Mitsudome T, Urayama T, Fujita S, Maeno Z, Mizugaki T, Jitsukawa K, Kaneda K. ChemCatChem, 2017, 9: 3632–3636

    Article  CAS  Google Scholar 

  11. Zhao TX, Zhai GW, Liang J, Li P, Hu XB, Wu YT. Chem Commun, 2017, 53: 8046–8049

    Article  CAS  Google Scholar 

  12. Schmid L, Canonica A, Baiker A. Appl Catal A-Gen, 2003, 255: 23–33

    Article  CAS  Google Scholar 

  13. Nguyen TVQ, Yoo WJ, Kobayashi S. Angew Chem Int Ed, 2015, 54: 9209–9212

    Article  CAS  Google Scholar 

  14. Jacquet O, Das Neves Gomes C, Ephritikhine M, Cantat T. J Am Chem Soc, 2012, 134: 2934–2937

    Article  CAS  PubMed  Google Scholar 

  15. Molla RA, Bhanja P, Ghosh K, Islam SS, Bhaumik A, Islam SM. ChemCatChem, 2017, 9: 1939–1946

    Article  CAS  Google Scholar 

  16. Cui X, Zhang Y, Deng Y, Shi F. Chem Commun, 2014, 50: 189–191

    Article  CAS  Google Scholar 

  17. Yang ZZ, Yu B, Zhang H, Zhao Y, Ji G, Liu Z. RSC Adv, 2015, 5: 19613–19619

    Article  CAS  Google Scholar 

  18. Federsel C, Boddien A, Jackstell R, Jennerjahn R, Dyson PJ, Scopelliti R, Laurenczy G, Beller M. Angew Chem Int Ed, 2010, 49: 9777–9780

    Article  CAS  Google Scholar 

  19. Zhang L, Han Z, Zhao X, Wang Z, Ding K. Angew Chem Int Ed, 2015, 54: 6186–6189

    Article  CAS  Google Scholar 

  20. Ju P, Chen J, Chen A, Chen L, Yu Y. ACS Sustain Chem Eng, 2017, 5: 2516–2528

    Article  CAS  Google Scholar 

  21. Bi QY, Lin JD, Liu YM, Xie SH, He HY, Cao Y. Chem Commun, 2014, 50: 9138–9140

    Article  CAS  Google Scholar 

  22. Zhang Y, Wang H, Yuan H, Shi F. ACS Sustain Chem Eng, 2017, 5: 5758–5765

    Article  CAS  Google Scholar 

  23. Liu H, Mei Q, Xu Q, Song J, Liu H, Han B. Green Chem, 2017, 19: 196–201

    Article  CAS  Google Scholar 

  24. Yang L, Zhao Y, Chen S, Wu Q, Wang X, Hu Z. Chin J Catal, 2013, 34: 1986–1991

    Article  CAS  Google Scholar 

  25. Kicinski W, Szala M, Bystrzejewski M. Carbon, 2014, 68: 1–32

    Article  CAS  Google Scholar 

  26. Li R, Wei Z, Gou X. ACS Catal, 2015, 5: 4133–4142

    Article  CAS  Google Scholar 

  27. Ma X, Ning G, Qi C, Xu C, Gao J. ACS Appl Mater Interfaces, 2014, 6: 14415–14422

    Article  CAS  PubMed  Google Scholar 

  28. Patel MA, Luo F, Khoshi MR, Rabie E, Zhang Q, Flach CR, Mendelsohn R, Garfunkel E, Szostak M, He H. ACS Nano, 2016, 10: 2305–2315

    Article  CAS  PubMed  Google Scholar 

  29. Wang S, Iyyamperumal E, Roy A, Xue Y, Yu D, Dai L. Angew Chem Int Ed, 2011, 50: 11756–11760

    Article  CAS  Google Scholar 

  30. Xu J, Zhao Y, Shen C, Guan L. ACS Appl Mater Interfaces, 2013, 5: 12594–12601

    Article  CAS  PubMed  Google Scholar 

  31. Yang S, Peng L, Huang P, Wang X, Sun Y, Cao C, Song W. Angew Chem Int Ed, 2016, 55: 4016–4020

    Article  CAS  Google Scholar 

  32. Modak A, Bhaumik A. J Mol Catal A-Chem, 2016, 425: 147–156

    Article  CAS  Google Scholar 

  33. Ma Z, Zhang H, Yang Z, Ji G, Yu B, Liu X, Liu Z. Green Chem, 2016, 18: 1976–1982

    Article  CAS  Google Scholar 

  34. Corma A, García H, Navarro MT, Palomares EJ, Rey F. Chem Mater, 2000, 12: 3068–3072

    Article  CAS  Google Scholar 

  35. Tanev PT, Chibwe M, Pinnavaia TJ. Nature, 1994, 368: 321–323

    Article  CAS  PubMed  Google Scholar 

  36. Li R, Cao A, Zhang Y, Li G, Jiang F, Li S, Chen D, Wang C, Ge J, Shu C. ACS Appl Mater Interfaces, 2014, 6: 20574–20578

    Article  CAS  PubMed  Google Scholar 

  37. Wen Z, Ci S, Hou Y, Chen J. Angew Chem Int Ed, 2014, 53: 6496–6500

    Article  CAS  Google Scholar 

  38. Yu J, Hai Y, Cheng B. J Phys Chem C, 2011, 115: 4953–4958

    Article  CAS  Google Scholar 

  39. Molla RA, Iqubal MA, Ghosh K, Islam SM. Green Chem, 2016, 18: 4649–4656

    Article  CAS  Google Scholar 

  40. Yang Z, Yu B, Zhang H, Zhao Y, Chen Y, Ma Z, Ji G, Gao X, Han B, Liu Z. ACS Catal, 2016, 6: 1268–1273

    Article  CAS  Google Scholar 

  41. Lai L, Potts JR, Zhan D, Wang L, Poh CK, Tang C, Gong H, Shen Z, Lin J, Ruoff RS. Energy Environ Sci, 2012, 5: 7936–7942

    Article  CAS  Google Scholar 

  42. Li Y, Zhao Y, Cheng H, Hu Y, Shi G, Dai L, Qu L. J Am Chem Soc, 2012, 134: 15–18

    Article  CAS  PubMed  Google Scholar 

  43. Luo Z, Lim S, Tian Z, Shang J, Lai L, MacDonald B, Fu C, Shen Z, Yu T, Lin J. J Mater Chem, 2011, 21: 8038–8044

    Article  CAS  Google Scholar 

  44. Perini L, Durante C, Favaro M, Agnoli S, Granozzi G, Gennaro A. Appl Catal B-Environ, 2014, 144: 300–307

    Article  CAS  Google Scholar 

  45. He DP, Jiang YL, Lv HF, Pan M, Mu SC. Appl Catal B-Environ, 2013, 132: 379–388

    Article  CAS  Google Scholar 

  46. Wertheim GK, Dicenzo SB. Phys Rev B, 1988, 37: 844–847

    Article  CAS  Google Scholar 

  47. Creutz C, Chou MH. J Am Chem Soc, 2009, 131: 2794–2795

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by the Chinese Academy of Sciences (QYZDY-SSW-SLH013) and the National Natural Science Foundation of China (21533011, 21503239).

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Authors and Affiliations

  1. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Colloid, Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China

    Xiaoying Luo, Hongye Zhang, Zhengang Ke, Cailing Wu, Shien Guo, Yunyan Wu, Bo Yu & Zhimin Liu

  2. University of Chinese Academy of Sciences, Beijing, 100049, China

    Xiaoying Luo, Zhengang Ke, Cailing Wu, Shien Guo, Yunyan Wu & Zhimin Liu

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  1. Xiaoying Luo
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  2. Hongye Zhang
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  3. Zhengang Ke
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  4. Cailing Wu
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  5. Shien Guo
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  6. Yunyan Wu
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  7. Bo Yu
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Correspondence to Zhimin Liu.

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Luo, X., Zhang, H., Ke, Z. et al. N-doped carbon supported Pd catalysts for N-formylation of amines with CO2/H2. Sci. China Chem. 61, 725–731 (2018). https://doi.org/10.1007/s11426-017-9215-2

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  • DOI: https://doi.org/10.1007/s11426-017-9215-2

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