Metal-Free Allylic Oxidation with Molecular Oxygen Catalyzed by g-C3N4 and N-Hydroxyphthalimide
Polymeric graphitic carbon nitride (g-C 3 N 4 ) is a layered graphite-like nitrogen-rich material, bearing the potential ability to reductively adsorb molecular oxygen for catalytic allylic oxidation. Furthermore, N -hydroxyphthalimide (NHPI) has been recognized as an efficient catalyst for aerobic...
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| Published in | Catalysis letters Vol. 144; no. 4; pp. 717 - 722 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
New York
Springer US
01.04.2014
Springer Springer Nature B.V |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Polymeric graphitic carbon nitride (g-C
3
N
4
) is a layered graphite-like nitrogen-rich material, bearing the potential ability to reductively adsorb molecular oxygen for catalytic allylic oxidation. Furthermore,
N
-hydroxyphthalimide (NHPI) has been recognized as an efficient catalyst for aerobic oxidation of various organic compounds under mild conditions in the presence of various co-catalysts. We present here a promising strategy for employing such nitride-rich g-C
3
N
4
combined with NHPI to form an all-organic metal-free composite and have examined its activity for allylic oxidation with molecular oxygen as the primary terminal oxidant. In the case of allylic oxidation α-isophorone catalyzed by g-C
3
N
4
/NHPI gave priority to its corresponding carbonyl compound and epoxide. The effects of various reaction conditions on the catalytic reaction were optimized, affording 74.8 % conversion with 44.4 % selectivity of ketoisophorone at 130 °C in 5 h. Repeated runs demonstrated that the catalyst was stable for at least three cycles without noticeable loss of its catalytic activity.
Graphical Abstract |
|---|---|
| AbstractList | Polymeric graphitic carbon nitride (g-C3N4) is a layered graphite-like nitrogen-rich material, bearing the potential ability to reductively adsorb molecular oxygen for catalytic allylic oxidation. Furthermore, N-hydroxyphthalimide (NHPI) has been recognized as an efficient catalyst for aerobic oxidation of various organic compounds under mild conditions in the presence of various co-catalysts. We present here a promising strategy for employing such nitride-rich g-C3N4 combined with NHPI to form an all-organic metal-free composite and have examined its activity for allylic oxidation with molecular oxygen as the primary terminal oxidant. In the case of allylic oxidation α-isophorone catalyzed by g-C3N4/NHPI gave priority to its corresponding carbonyl compound and epoxide. The effects of various reaction conditions on the catalytic reaction were optimized, affording 74.8 % conversion with 44.4 % selectivity of ketoisophorone at 130 °C in 5 h. Repeated runs demonstrated that the catalyst was stable for at least three cycles without noticeable loss of its catalytic activity.Graphical Abstract Polymeric graphitic carbon nitride (g-C 3 N 4 ) is a layered graphite-like nitrogen-rich material, bearing the potential ability to reductively adsorb molecular oxygen for catalytic allylic oxidation. Furthermore, N -hydroxyphthalimide (NHPI) has been recognized as an efficient catalyst for aerobic oxidation of various organic compounds under mild conditions in the presence of various co-catalysts. We present here a promising strategy for employing such nitride-rich g-C 3 N 4 combined with NHPI to form an all-organic metal-free composite and have examined its activity for allylic oxidation with molecular oxygen as the primary terminal oxidant. In the case of allylic oxidation α-isophorone catalyzed by g-C 3 N 4 /NHPI gave priority to its corresponding carbonyl compound and epoxide. The effects of various reaction conditions on the catalytic reaction were optimized, affording 74.8 % conversion with 44.4 % selectivity of ketoisophorone at 130 °C in 5 h. Repeated runs demonstrated that the catalyst was stable for at least three cycles without noticeable loss of its catalytic activity. Graphical Abstract |
| Author | Tang, Ruiren Wang, Zhen Liu, Guiyin |
| Author_xml | – sequence: 1 givenname: Guiyin surname: Liu fullname: Liu, Guiyin organization: School of Chemistry and Chemical Engineering, Central South University – sequence: 2 givenname: Ruiren surname: Tang fullname: Tang, Ruiren email: trr@mail.csu.edu.cn organization: School of Chemistry and Chemical Engineering, Central South University – sequence: 3 givenname: Zhen surname: Wang fullname: Wang, Zhen organization: School of Chemistry and Chemical Engineering, Central South University |
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| Cites_doi | 10.1002/anie.201004365 10.1134/1.1262418 10.1039/b408974j 10.1021/ja102866p 10.1002/adsc.201100175 10.1002/anie.201101182 10.1021/cs300413x 10.1016/j.cclet.2013.01.030 10.5012/bkcs.2010.31.6.1723 10.1016/j.molcata.2010.01.003 10.1007/s10904-012-9666-z 10.1016/j.catcom.2009.09.019 10.1002/anie.200903886 10.1007/s00339-011-6471-4 10.1039/b813019a 10.1016/j.ijhydene.2011.09.072 10.1016/j.jcat.2012.02.015 10.1016/j.catcom.2006.10.037 10.1002/adsc.200900509 10.3762/bjoc.9.146 10.1007/s10562-013-1002-x 10.1016/j.apcata.2005.11.015 10.1016/S0040-4039(99)01494-X 10.1039/b915737a 10.1039/c2cc32181e 10.1016/j.jcat.2005.08.001 10.1021/ja809307s 10.1039/c2cp42484c 10.1080/00397910802484114 10.5012/bkcs.2012.33.2.459 10.3866/PKU.WHXB201209104 |
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| Keywords | Molecular oxygen Allylic oxidation g-C N Hydroxyphthalimide Heterogeneous catalysis Oxygen Catalytic reaction Oxidation N-Hydroxyphthalimide |
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| Snippet | Polymeric graphitic carbon nitride (g-C
3
N
4
) is a layered graphite-like nitrogen-rich material, bearing the potential ability to reductively adsorb... Polymeric graphitic carbon nitride (g-C3N4) is a layered graphite-like nitrogen-rich material, bearing the potential ability to reductively adsorb molecular... |
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| SubjectTerms | Carbon nitride Carbonyl compounds Carbonyls Catalysis Catalysts Catalytic activity Catalytic converters Chemistry Chemistry and Materials Science Exact sciences and technology General and physical chemistry Industrial Chemistry/Chemical Engineering Nitrogen Organic compounds Organometallic Chemistry Oxidation Oxygen Physical Chemistry Selectivity Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
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| Title | Metal-Free Allylic Oxidation with Molecular Oxygen Catalyzed by g-C3N4 and N-Hydroxyphthalimide |
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