Solvent and additive-free selective aerobic allylic hydroxylation of β-pinene catalyzed by metalloporphyrins
- Corresponding author: Zhao Zhen-Dong, zdzhao@189.cn
Citation:
Xu Shi-Chao, Zhu Shou-Ji, Bi Liang-Wu, Chen Yu-Xiang, Wang Jing, Lu Yan-Ju, Gu Yan, Zhao Zhen-Dong. Solvent and additive-free selective aerobic allylic hydroxylation of β-pinene catalyzed by metalloporphyrins[J]. Chinese Chemical Letters,
;2017, 28(3): 575-578.
doi:
10.1016/j.cclet.2016.11.020
Carari D.M., da Silva M.J.. Fe (NO3)3-catalyzed monoterpene oxidation by hydrogen peroxide:an inexpensive and environmentally benign oxidative process[J]. Catal. Lett., 2014,144:615-622. doi: 10.1007/s10562-013-1189-x
Fang C., Dai J., Xu H., Guo Q., Fu Y.. Iron-catalyzed selective oxidation of 5-hydroxylmethylfurfural in air:a facile synthesis of 2, 5-diformylfuran at room temperature[J]. Chin. Chem. Lett., 2015,26:1265-1268. doi: 10.1016/j.cclet.2015.07.001
Rachwalik R., Hunger M., Sulikowski B.. Transformations of monoterpene hydrocarbons on ferrierite type zeolites[J]. Appl. Catal. A, 2012,427:98-105.
Neuenschwander U., Meier E., Hermans I.. Peculiarities of b-pinene autoxidation[J]. ChemSusChem, 2011,4:1613-1621. doi: 10.1002/cssc.v4.11
de Paula F.G.F., Berllini L., da Silva M.J.. A novel Fe (Ⅲ) salt-catalyzed monoterpene aerobic oxidation in methyl alcohol[J]. Catal. Commun., 2013,42:129-133. doi: 10.1016/j.catcom.2013.08.018
da Silva M.J., Robles-Dutenhefner P., Menini L., Gusevskaya E.V.. Cobalt catalyzed autoxidation of monoterpenes in acetic acid and acetonitrile solutions[J]. J. Mol. Catal. A, 2003,201:71-77. doi: 10.1016/S1381-1169(03)00180-8
Jadhav S.V., Jinka K.M., Bajaj H.C.. Nanosized sulfated zinc ferrite as catalyst forthe synthesis of nopol and other fine chemicals[J]. Catal. Today, 2012,198:98-105. doi: 10.1016/j.cattod.2012.01.028
Skočibušić M., Bezić N., Dunkić V.. Phytochemical composition and antimicrobial activities of the essential oils from Satureja subspicata Vis. growing in Croatia[J]. Food Chem., 2006,96:20-28. doi: 10.1016/j.foodchem.2005.01.051
Bakkali F., Averbeck S., Averbeck D., Idaomar M.. Biological effects of essential oils-a review[J]. Food Chem. Toxicol., 2008,46:446-475. doi: 10.1016/j.fct.2007.09.106
Joshel L.M., Palkin S.. The oxidation of & pinene with selenium dioxide[J]. J. Am. Chem. Soc., 1942,64:1008-1009. doi: 10.1021/ja01256a503
Menini L., da Silva M.J., Lelis M.F.F.. Novel solvent free liquid-phase oxidation of b-pinene over heterogeneous catalysts based on Fe3-XMXO4(M=Co and Mn)[J]. Appl. Catal. A, 2004,269:117-121. doi: 10.1016/j.apcata.2004.04.005
Jin J., Shen M.. Progress in oxidation of b-pinene[J]. Guangzhou Chem., 2006,31:51-56.
Yi S., Li M., Hu X., Mo W., Shen Z.. An efficient and convenient method for the preparation of disulfides from thiols using oxygen as oxidant catalyzed by tertbutyl nitrite[J]. Chin. Chem. Lett., 2016,27:1505-1508. doi: 10.1016/j.cclet.2016.03.016
Thao N.T., Trung H.H.. Selective oxidation of styrene over Mg-Co-Al hydrotalcite like-catalysts using air as oxidant[J]. Catal. Commun., 2014,45:153-157. doi: 10.1016/j.catcom.2013.11.004
Meunier B.. Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage[J]. Chem. Rev., 1992,92:1411-1456. doi: 10.1021/cr00014a008
Che C.M., Lo V.K.Y., Zhou C.Y., Huang J.S.. Selective functionalisation of saturated C H bonds with metalloporphyrin catalysts[J]. Chem. Soc. Rev., 2011,40:1950-1975. doi: 10.1039/c0cs00142b
Li X.D., Zhu Y.C., Yang L.J.. Crown ether-appended Fe (Ⅲ) porphyrin:synthesis, characterization and catalytic oxidation of cyclohexene with molecular oxygen[J]. Chin. Chem. Lett., 2012,23:375-378. doi: 10.1016/j.cclet.2011.12.011
Liu Q., Guo C.C.. Theoretical studies and industrial applications of oxidative activation of inert C-H bond by metalloporphyrin-based biomimetic catalysis[J]. Sci. China Ser. B Chem., 2012,55:2036-2053. doi: 10.1007/s11426-012-4739-y
Xu S.C., Zhao Z.D., Bi L.W.. Selective aerobic hydroxylation of p-menthane to dihydroterpineols catalyzed by metallopor-phyrins in solvent and additive free system[J]. Catal. Commun., 2015,59:26-29. doi: 10.1016/j.catcom.2014.09.039
Zhou W.Y., Hu B.C., Liu Z.L.. Metallo-deuteroporphyrin complexes derived from heme:a homogeneous catalyst for cyclohexane oxidation[J]. Appl. Catal. A, 2009,358:136-140. doi: 10.1016/j.apcata.2009.02.003
Guo C.C., Yang W.J., Miao Y.L.. Selectively aerobic oxidation of C=C and allylic C-H bonds in (a-pinene over simple metalloporphyrins[J]. J. Mol. Catal. A, 2005,226:279-284. doi: 10.1016/j.molcata.2004.10.049
Neuenschwander U., Guignard F., Hermans I.. Mechanism of the aerobic oxidation of a-pinene[J]. ChemSusChem, 2010,3:75-84. doi: 10.1002/cssc.v3:1
Bach R.D., Dmitrenko O.. The somersault mechanism for the P-450 hydroxylation of hydrocarbons The intervention of transient inverted metastable hydroperoxides[J]. J. Am. Chem. Soc., 2006,128:1474-1488. doi: 10.1021/ja052111+
Xu S.C., Liu W.W., Hu B.C., Cao W., Liu Z.L.. Biomimetic enhanced chemiluminescence of luminol-H2O2 system by manganese (Ⅲ) deuteroporphyrin and its application in flow injection determination of phenol at trace level[J]. J. Photochem. Photobiol. A Chem., 2012,227:32-37. doi: 10.1016/j.jphotochem.2011.10.021
Sun C.G., Zhou W.Y., Hu B.C., Xu S.C., Liu Z.L.. A facile synthesis of 2, 7, 12, 18-tetramethyl-13, 17-di (3-hydroxypropyl) porphyrin[J]. Fine Chem., 2009,26:919-922, 927.
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