Magnetically Separable Microporous Fe-Porphyrin Networks for Catalytic Carbene Insertion into N-H Bonds

ACS Catalysis

Volumn 5, Issue 1, 2015, Pages 350-355

  Yoo, Jin ^a   Park, Nojin ^a   Park, Joon Hyun ^a   Park, Ji Hoon ^a   Kang, Sungah ^a   Lee, Sang Moon ^a   Kim, Hae Jin ^b   Jo, Hyein ^c   Park, Je Geun ^c   Son, Seung Uk ^a  

^a Sungkyunkwan University   (South Korea)

^b Korea Basic Science Institute (KBSI)   (South Korea)

^c Seoul National University   (South Korea)

Author keywords

carbene insertion; iron; magnetic nanocatalyst; microporous organic polymer; porphyrin

Indexed keywords

COATINGS; IRON; MAGNETIC SEPARATION; MICROPOROSITY; NANOPARTICLES; ORGANIC COMPOUNDS; ORGANIC POLYMERS; POROUS MATERIALS; PORPHYRINS; X RAY DIFFRACTION;

CARBENE INSERTION; CATALYTIC PERFORMANCE; HOMOGENEOUS COATINGS; MAGNETIC NANOCATALYST; MAGNETICALLY SEPARABLE; MICROPOROUS ORGANIC POLYMERS; POWDER X RAY DIFFRACTION; SONOGASHIRA COUPLING;

MICROPOROUS MATERIALS;

EID: 84927716559     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs501378j     Document Type: Article

References (83)

1. Wang, D.; Astruc, D. Chem. Rev. 2014, 114, 6949 - 6985 10.1021/cr500134h
2. Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.-M. Chem. Rev. 2011, 111, 3036 - 3075 10.1021/cr100230z
3. Shylesh, S.; Schünemann, V.; Thiel, W. R. Angew. Chem., Int. Ed. 2010, 49, 3428 - 3459 10.1002/anie.200905684
4. Hu, A.; Yee, G. T.; Lin, W. J. Am. Chem. Soc. 2005, 127, 12486 - 12487 10.1021/ja053881o
5. Ding, S.; Xing, Y.; Radosz, M.; Shen, Y. Macromolecules 2006, 39, 6399 - 6405 10.1021/ma061062y
6. Li, P.; Wang, L.; Zhang, L.; Wang, G.-W. Adv. Synth. Catal. 2012, 354, 1307 - 1318 10.1002/adsc.201100725
7. Wittmann, S.; Schätz, A.; Grass, R. N.; Stark, W. J.; Reiser, O. Angew. Chem., Int. Ed. 2010, 49, 1867 - 1870 10.1002/anie.200906166
8. Keller, M.; Collière, V.; Reiser, O.; Caminade, A.-M.; Majoral, J.-P.; Quali, A. Angew. Chem., Int. Ed. 2013, 52, 3626 - 3629 10.1002/anie.201209969
9. Grass, R. N.; Athanassiou, E. K.; Stark, W. J. Angew. Chem., Int. Ed. 2007, 46, 4909 - 4912 10.1002/anie.200700613
10. Schätz, A.; Grass, R. N.; Stark, W. J.; Reiser, O. Chem. Eur. J. 2008, 14, 8262 - 8266 10.1002/chem.200801001
11. Schätz, A.; Grass, R. N.; Kainz, Q.; Stark, W. J.; Reiser, O. Chem. Mater. 2010, 22, 305 - 310 10.1021/cm9019099
12. Kainz, Q. M.; Linhardt, R.; Maity, P. K.; Hanson, P. R.; Reiser, O. ChemSusChem 2013, 6, 721 - 729 10.1002/cssc.201200453
13. Schätz, A.; Long, T. R.; Grass, R. N.; Stark, W. J.; Hanson, P. R.; Reiser, O. Adv. Funct. Mater. 2010, 20, 4323 - 4328 10.1002/adfm.201000959
14. Zhu, M.; Diao, G. J. Phys. Chem. C 2011, 115, 24743 - 24749 10.1021/jp206116e
15. Linhardt, R.; Kainz, Q. M.; Grass, R. N.; Stark, W. J.; Reiser, O. RSC Adv. 2014, 4, 8541 - 8549 10.1039/c3ra46946h
16. Kainz, Q. M.; Linhardt, R.; Grass, R. N.; Vilé, G.; Pérez-Ramírez, J.; Stark, W. J.; Reiser, O. Adv. Funct. Mater. 2014, 24, 2020 - 2027 10.1002/adfm.201303277
17. Laska, U.; Frost, C. G.; Price, G. J.; Plucinski, P. K. J. Catal. 2009, 268, 318 - 328 10.1016/j.jcat.2009.10.001
18. Kim, Y.; Kim, M.-J. Bull. Korean Chem. Soc. 2010, 31, 1368 - 1370 10.5012/bkcs.2010.31.5.1368
19. Stevens, P. D.; Fan, J.; Gardimalla, H. M. R.; Yen, M.; Gao, Y. Org. Lett. 2005, 7, 2085 - 2088 10.1021/ol050218w
20. Kainz, Q. M.; Reiser, O. Acc. Chem. Res. 2014, 47, 667 - 677 10.1021/ar400236y
21. Yang, X.; Li, B.; Majeed, I.; Liang, L.; Long, X.; Tan, B. Polym. Chem. 2013, 4, 1425 - 1429 10.1039/c2py20999c
22. Dawson, R.; Cooper, A. I.; Adams, D. J. Prog. Polym. Sci. 2012, 37, 530 - 563 10.1016/j.progpolymsci.2011.09.002
23. Vilela, F.; Zhang, K.; Antonietti, M. Energy Environ. Sci. 2012, 5, 7819 - 7832 10.1039/c2ee22002d
24. Zhang, Y.; Riduan, S. N. Chem. Soc. Rev. 2012, 41, 2083 - 2094 10.1039/c1cs15227k
25. Cooper, A. I. Adv. Mater. 2009, 21, 1291 - 1295 10.1002/adma.200801971
26. Thomas, A. Angew. Chem., Int. Ed. 2010, 49, 8328 - 8344 10.1002/anie.201000167
27. Maly, K. E. J. Mater. Chem. 2009, 19, 1781 - 1787 10.1039/b816089a
28. Weder, C. Angew. Chem., Int. Ed. 2008, 47, 448 - 450 10.1002/anie.200704697
29. McKeown, N. B.; Budd, P. M. Chem. Soc. Rev. 2006, 35, 675 - 683 10.1039/b600349d
30. Thiel, K.; Zehbe, R.; Roeser, J.; Strauch, P.; Enthaler, S.; Thomas, A. Polym. Chem. 2013, 4, 1848 - 1856 10.1039/c2py20947k
31. Bleschke, C.; Schmidt, J.; Kundu, D. S.; Blechert, S.; Thomas, A. Adv. Synth. Catal. 2011, 353, 3101 - 3106 10.1002/adsc.201100674
32. Du, X.; Sun, Y.; Tan, B.; Teng, Q.; Yao, X.; Su, C.; Wang, W. Chem. Commun. 2010, 46, 970 - 972 10.1039/b920113k
33. Ma, H.; Ren, H.; Meng, S.; Sun, F.; Zhu, G. Sci. Rep. 2013, 3, 2611 - 2614 10.1038/srep02611
34. Neti, V. S. P. K.; Wu, X.; Deng, S.; Echegoyen Polym. Chem. 2013, 4, 4566 - 4569 10.1039/c3py00798g
35. Wang, X.-S.; Liu, J.; Bonefont, J. M.; Yuan, D.-Q.; Thallapally, P. K.; Ma, S. Chem. Commun. 2013, 49, 1533 - 1535 10.1039/c2cc38067f
36. Totten, R. K.; Kim, Y.-S.; Weston, M. H.; Farha, O. K.; Hupp, J. T.; Nguyen, S. T. J. Am. Chem. Soc. 2013, 135, 11720 - 11723 10.1021/ja405495u
37. Saha, B.; Gupta, D.; Abu-Omar, M. M.; Modak, A.; Bhaumik, A. J. Catal. 2013, 299, 316 - 320 10.1016/j.jcat.2012.12.024
38. Modak, A.; Nandi, M.; Mondal, J.; Bhaumik, A. Chem. Commun. 2012, 48, 248 - 250 10.1039/c1cc14275e
39. Chen, L.; Yang, Y.; Guo, Z.; Jiang, D. Adv. Mater. 2011, 23, 3149 - 3154 10.1002/adma.201100974
40. Shultz, A. M.; Farha, O. K.; Hupp, J. T.; Nguyen, S. T. Chem. Sci. 2011, 2, 686 - 689 10.1039/c0sc00339e
41. Chen, L.; Yang, Y.; Jiang, D. J. Am. Chem. Soc. 2010, 132, 9138 - 9143 10.1021/ja1028556
42. Mackintosh, H. J.; Budd, P. M.; McKeown, N. B. J. Mater. Chem. 2008, 18, 573 - 578 10.1039/b715660j
43. Ferrand, Y.; Maux, P. L.; Simonneaux, G. Tetrahedron: Asymmetry 2005, 16, 3829 - 3836 10.1016/j.tetasy.2005.10.021
44. Kadish, K. M.; Smith, K. M.; Guilard, R. The Porphyrin Handbook; Academic Press: San Diego, CA, 2000.
45. Galardon, E.; Le Maux, P.; Simonneaux, G. J. Chem. Soc., Perkin Trans. 1 1997, 2455 - 2456 10.1039/a704687a
46. Galardon, E.; Le Maux, P.; Simonneaux, G. Tetrahedron 2000, 56, 615 - 621 10.1016/S0040-4020(99)01050-9
47. Mirafzal, B. A.; Cheng, G.; Woo, L. K. J. Am. Chem. Soc. 2002, 124, 176 - 177 10.1021/ja016721v
48. Chen, Y.; Huang, L.; Zhang, X. P. Org. Lett. 2003, 5, 2493 - 2496 10.1021/ol0347444
49. Rose, E.; Ren, P.-Z.; Andrioletti, B. Chem.-Eur. J. 2004, 10, 224 - 230 10.1002/chem.200305222
50. Vyas, R.; Gao, G.-Y.; Harden, J. D.; Zhang, X. P. Org. Lett. 2004, 6, 1907 - 1910 10.1021/ol049691k
51. Gopalaiah, K. Chem. Rev. 2013, 113, 3248 - 3296 10.1021/cr300236r
52. Jiang, J.-X.; Su, F.; Trewin, A.; Wood, C. D.; Campbell, N. L.; Niu, H.; Dickinson, C.; Ganin, A. Y.; Rosseinsky, M. J.; Khimyak, Y. Z.; Cooper, A. I. Angew. Chem., Int. Ed. 2007, 46, 8574 - 8578 10.1002/anie.200701595
53. Jiang, J.-X.; Su, F.; Trewin, A.; Wood, C. D.; Niu, H.; Jones, J. T. A.; Khimyak, Y. Z.; Cooper, A. I. J. Am. Chem. Soc. 2008, 130, 7710 - 7722 10.1021/ja8010176
54. Jiang, J.-X.; Laybourn, A.; Clowes, R.; Khimyak, Y. Z.; Bacsa, J.; Higgins, S. J.; Adams, D. J.; Cooper, A. I. Macromolecules 2010, 43, 7577 - 7582 10.1021/ma101468r
55. Cho, H. C.; Lee, H. S.; Chun, J.; Lee, S. M.; Kim, H. J.; Son, S. U. Chem. Commun. 2011, 47, 917 - 919 10.1039/c0cc03914d
56. Chun, J.; Park, J. H.; Kim, J.; Lee, S. M.; Kim, H. J.; Son, S. U. Chem. Mater. 2012, 24, 3458 - 3463 10.1021/cm301786g
57. Lee, H. S.; Choi, J.; Jin, J.; Chun, J.; Lee, S. M.; Kim, H. J.; Son, S. U. Chem. Commun. 2012, 48, 94 - 96 10.1039/c1cc15535k
58. Kang, N.; Park, J. H.; Choi, J.; Jin, J.; Chun, J.; Jung, I. G.; Jeong, J.; Park, J.-G.; Lee, S. M.; Kim, H. J.; Son, S. U. Angew. Chem., Int. Ed. 2012, 51, 6626 - 6630 10.1002/anie.201202244
59. Kang, N.; Park, J. H.; Ko, K. C.; Chun, J.; Kim, E.; Shin, H. W.; Lee, S. M.; Kim, H. J.; Ahn, T. K.; Lee, J. Y.; Son, S. U. Angew. Chem., Int. Ed. 2013, 52, 6228 - 6232 10.1002/anie.201300655
60. Chun, J.; Kang, S.; Lee, S. M.; Kim, H. J.; Son, S. U. J. Mater. Chem. A 2013, 1, 5517 - 5523 10.1039/c3ta10477j
61. Park, J. H.; Ko, K. C.; Park, N.; Shin, H.-W.; Kim, E.; Kang, N.; Ko, J. H.; Lee, S. M.; Kim, H. J.; Ahn, T. K.; Lee, J. Y.; Son, S. U. J. Mater. Chem. A 2014, 2, 7656 - 7661 10.1039/c4ta00989d
62. Kang, N.; Park, J. H.; Jin, M.; Park, N.; Lee, S. M.; Kim, H. J.; Kim, J. M.; Son, S. U. J. Am. Chem. Soc. 2013, 135, 19115 - 19118 10.1021/ja411263h
63. Chun, J.; Kang, S.; Park, N.; Park, E. J.; Jin, X.; Kim, K.-D.; Seo, H. O.; Lee, S. M.; Kim, H. J.; Kwon, W. H.; Park, Y.-K.; Kim, J. M.; Kim, Y. D.; Son, S. U. J. Am. Chem. Soc. 2014, 136, 6786 - 6789 10.1021/ja500362w
64. Lim, B.; Jin, J.; Yoo, J.; Han, S. Y.; Kim, K.; Kang, S.; Park, N.; Lee, S. M.; Kim, H. J.; Son, S. U. Chem. Commun. 2014, 50, 7723 - 7726 10.1039/c4cc02068e
65. Drouet, S.; Merhi, A.; Yao, D.; Cifuentes, M. P.; Humphrey, M. G.; Wielgus, M.; Olesiak-Banska, J.; Matczyszyn, K.; Samoc, M.; Paul, F.; Paul-Roth, C. O. Tetrahedron 2012, 68, 10351 - 10359 10.1016/j.tet.2012.09.108
66. Sun, Z.-C.; She, Y.-B.; Zhou, Y.; Song, X.-F.; Li, K. Molecules 2011, 16, 2960 - 2970 10.3390/molecules16042960
67. Delapierre, G.; Duclairoir, F.; Marchon, J.-C. PCT Int. Appl. WO 2007048924, 2007.
68. Skrzypek, D.; Madejska, I.; Habdas, J. J. Phys. Chem. Solids 2005, 66, 91 - 97 10.1016/j.jpcs.2004.07.008
69. Ge, J.; Yin, Y. Adv. Mater. 2008, 20, 3485 - 3491 10.1002/adma.200800657
70. Baumann, L. K.; Mbuvi, H. M.; Du, G.; Woo, L. K. Organometallics 2007, 26, 3995 - 4002 10.1021/om0610997
71. Aviv, I.; Gross, Z. Synlett 2006, 6, 951 10.1055/s-2006-939035
72. Aiv, I.; Gross, Z. Chem. Eur. J. 2008, 14, 3995 - 4005 10.1002/chem.200701885
73. It should be noted that the 6 N HCl solution has been used in the workup process for Fe-porphyrin complexes (see the Experimental Section and ref 19b). The retention of FeIIICl in porphyrin moieties of H-FePN during the etching process of inner Fe3O4 materials was further confirmed by the absence of a Q band at 660 nm (absorption band of the metal-free porphyrin moiety) in reflectance spectroscopy of H-FePN.
74. Zhu, Z.; Espenson, J. H. J. Am. Chem. Soc. 1996, 118, 9901 - 9907 10.1021/ja954039t
75. Yang, M.; Wang, X.; Li, H.; Livant, P. J. Org. Chem. 2001, 66, 6729 - 6733 10.1021/jo010583a
76. Morilla, M. E.; Díaz-Requejo, M. M.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Peréz, P. J. Chem. Commun. 2002, 2998 - 2999 10.1039/b207389g
77. Anding, B. J.; Woo, L. K. Organometallics 2013, 32, 2599 - 2607 10.1021/om400098v
78. Xu, B.; Zhu, S.-F.; Zuo, X.-D.; Zhang, Z.-C.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2014, 53, 3913 - 3916 10.1002/anie.201400236
79. In screening the solvent, the reactions showed 100%, 80%, and 49% conversion of EDA in methylene chloride, hexane, and tolune, respectively. When tert -butyl diazoacetate was used instead of EDA, the conversion was 32% in acetone after 20 min.
80. When 1 mol % of the monomer (FeIIICl-5,10,15,20-tetrakis(4-ethynylphenyl)porphyrin) was used in acetone instead of Fe3O4@ FePMN, the reactions showed 63% and 100% conversion of EDA after 1 and 3 min, respectively.
81. Kadish, K. M.; Bottomley, L. A.; Brace, J. G.; Winograd, N. J. Am. Chem. Soc. 1980, 102, 4341 - 4344 10.1021/ja00533a008
82. Grosvenor, A. P.; Kobe, B. A.; Biesinger, M. C.; McIntyre, N. S. Surf. Interface Anal. 2004, 36, 1564 - 1574 10.1002/sia.1984
83. The detection limit (0.2 ppm) for Fe ions corresponds to 0.0005 times the amount of Fe in the catalyst used.