Rapid transformation of benzylic alcohols to aldehyde in the presence of cucurbit[8]uril

被引:29
作者
Cong Hang [1 ,2 ]
Zhao Fang-fang [1 ]
Zhang Jian-xin [3 ]
Zeng Xi [2 ]
Tao Zhu [1 ,2 ]
Xue Sai-feng [2 ]
Zhu Qian-jiang [2 ]
机构
[1] Guizhou Univ, Inst Appl Chem, Guiyang 550025, Peoples R China
[2] Guizhou Univ, Key Lab Macrocycl & Supramol Chem Guizhou Prov, Guiyang 550025, Peoples R China
[3] Key Lab Chem Nat Prod Guizhou Prov, Guiyang 550002, Peoples R China
关键词
Cucurbituril; Catalysis; Veratryl alcohol; IBX; Supramolecular; CUCURBITURIL; OXIDATION; CYCLODEXTRIN; ACIDS;
D O I
10.1016/j.catcom.2009.09.018
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Heterogeneous catalytic oxidation of veratryl alcohol to veratryaldehyde with o-iodoxybenzoic acid (IBX) in the presence of cucurbit[8]uril (Q[8]) has been investigated. The evidence of oxidation kinetics affirmed the supramolecular catalysis of Q[8]. Experimental investigation of addition of catalyst and the initial pH suggested that the optimum proportion of reagents is a 0.1:1:1 M ratio (Q[8]:alcohol: IBX) and neutral pH value. The screening of macrocycles, such as cucurbiturils and cyclodextrins, indicated the obvious dependence of catalytic activity on the cavity size and chemical structure of catalysts. The Q[8]catalytic transformation of benzyl alcohol and 3-methoxybenzyl alcohol exhibited a very satisfying conversion. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:167 / 170
页数:4
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