Hua-Jie Zhu
Kunming Institute of Botany
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Featured researches published by Hua-Jie Zhu.
Synthetic Communications | 2003
Hua-Jie Zhu; Charles U. Pittman
Abstract Aromatic esters, including the extremely sterically hindered ester: t-amyl 2-chlorobenzoate, are readily reduced to the corresponding benzyl alcohols in high yield with NaBH4 in refluxing diglyme (162°C). In sharp contrast, aliphatic esters usually gave only low yields of alcohols. Instead, diglyme fragmentation products are formed which undergo transesterification reactions, producing complex product mixtures including products such as RCOOCH2CH2OCH3. The mechanism of this process involves sodium borohydride-induced SN2 cleavage of diglyme (hydride attack) at high temperatures. However, when the extremely electron rich, 3,4,5-trimethoxybenzoic acid is treated with NaBH4/diglyme at 162°C (with or without an equivalent of LiCl), no 3,4,5-trimethyoxybenzyl alcohol is formed. The electron rich and hindered ester, t-amyl-3,4,5-trimethoxybenzoate, also does not reduce under these conditions (with or without LiCl). However, both methyl and isopropyl 3,4,5-trimethoxybenzoate esters were converted into 3,4,5-trimethyoxybenzyl alcohol in good yields in NaBH4/diglyme/LiCl at 162°C. These reductions did not occur unless LiCl was present, illustrating the electron releasing effect of the three methoxy functions which reduce the carbonyl groups reactivity.
New Journal of Chemistry | 2003
Hua-Jie Zhu; Kai-Tao Lu; Guang-Ri Sun; Jinbao He; Haiqing Li; Charles U. Pittman
High temperature (162°C) reductions of aromatic amides were studied to extend the useful range of functional group transformations by NaBH4. Primary aromatic amides were reduced to the amines with NaBH4–diglyme at 162°C. Reduction proceeds via fast initial loss of hydrogen, followed by formation of the corresponding nitrile, which is then more slowly reduced to the amine. N-Methylbenzamide is not reduced under these conditions, but it is reduced to benzylmethylamine when LiCl is added to NaBH4–diglyme at 162°C. LiCl addition raised the rate of primary aromatic amide and aromatic nitrile conversions to both the nitrile, first, and the amine. An intermediate was isolated from the reaction of N-benzylformamide with NaBH4–LiCl in diglyme at 162°C. It was examined by 1H NMR, atomic absorption, IR and thermal decomposition. Possible structures are proposed. A mechanism for the reduction of primary aromatic amides is proposed based on the initial evolution of one mole equivalent of hydrogen and formation of the nitrile prior to further reduction to amine.
European Journal of Organic Chemistry | 2009
Jie Ren; Ju-Xing Jiang; Liang-Bo Li; Tou-Geng Liao; Ren-Rong Tian; Xu-Lin Chen; Si-Ping Jiang; Charles U. Pittman; Hua-Jie Zhu
European Journal of Organic Chemistry | 2007
Liang‐Chun Li; Jie Ren; Tou-Gen Liao; Ju-Xing Jiang; Hua-Jie Zhu
European Journal of Organic Chemistry | 2006
Liang‐Chun Li; Ju-Xing Jiang; Jie Ren; Yi Ren; Charles U. Pittman; Hua-Jie Zhu
Journal of Molecular Structure-theochem | 2005
Hua-Jie Zhu; Yi Ren; Jie Ren; San-Yan Chu
Tetrahedron-asymmetry | 2008
Tougen Liao; Jie Ren; Hua-Fang Fan; Ming-Jin Xie; Hua-Jie Zhu
Journal of Molecular Structure-theochem | 2004
Hua-Jie Zhu; Yi Ren; Jie Ren
European Journal of Organic Chemistry | 2006
Jie Ren; Liang‐Chun Li; Ji‐Kai Liu; Hua-Jie Zhu; Charles U. Pittman
Archive | 2010
Hua-Jie Zhu; Jie Ren; Ju-Xing Jiang