Oxidation of Aromatic Aldehydes to Esters: A Sulfate Radical Redox System

Ya Fei Guo; Sajid Mahmood; Bao Hua Xu; Xiao Qian Yao; Hong Yan He; Suo Jiang Zhang

doi:10.1021/acs.joc.6b02775

Oxidation of Aromatic Aldehydes to Esters: A Sulfate Radical Redox System

Ya Fei Guo, Sajid Mahmood, Bao Hua Xu^*, Xiao Qian Yao, Hong Yan He, Suo Jiang Zhang

^*此作品的通讯作者

科研成果: 期刊稿件 › 文章 › 同行评审

24 引用（Scopus）

摘要

A mild oxidative esterification of various aromatic aldehydes by sulfate radical redox system was presented. In the reaction pathway exploration, the transiency of MeOSO₃^- was disclosed, which was generated from esterification between the in situ generated HSO₄^- and MeOH, a rate-limiting step in the process. More importantly, the selectivity-controlling step was represented by the subsequent nucleophilic displacement between MeOSO₃^- and aldehydes. The ionic oxidant 1a ((NH₄)₂S₂O₈) with more N-H numbers in the cation, as compared with 1c ((n-Bu₄N)₂S₂O₈) and 1d ((PyH)₂S₂O₈), has better performance in the oxidative esterification of aldehydes.

源语言	英语
页（从-至）	1591-1599
页数	9
期刊	Journal of Organic Chemistry
卷	82
期	3
DOI	https://doi.org/10.1021/acs.joc.6b02775
出版状态	已出版 - 3 2月 2017
已对外发布	是

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title = "Oxidation of Aromatic Aldehydes to Esters: A Sulfate Radical Redox System",

abstract = "A mild oxidative esterification of various aromatic aldehydes by sulfate radical redox system was presented. In the reaction pathway exploration, the transiency of MeOSO3- was disclosed, which was generated from esterification between the in situ generated HSO4- and MeOH, a rate-limiting step in the process. More importantly, the selectivity-controlling step was represented by the subsequent nucleophilic displacement between MeOSO3- and aldehydes. The ionic oxidant 1a ((NH4)2S2O8) with more N-H numbers in the cation, as compared with 1c ((n-Bu4N)2S2O8) and 1d ((PyH)2S2O8), has better performance in the oxidative esterification of aldehydes.",

author = "Guo, {Ya Fei} and Sajid Mahmood and Xu, {Bao Hua} and Yao, {Xiao Qian} and He, {Hong Yan} and Zhang, {Suo Jiang}",

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doi = "10.1021/acs.joc.6b02775",

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T1 - Oxidation of Aromatic Aldehydes to Esters

T2 - A Sulfate Radical Redox System

AU - Guo, Ya Fei

AU - Mahmood, Sajid

AU - Xu, Bao Hua

AU - Yao, Xiao Qian

AU - He, Hong Yan

AU - Zhang, Suo Jiang

PY - 2017/2/3

Y1 - 2017/2/3

N2 - A mild oxidative esterification of various aromatic aldehydes by sulfate radical redox system was presented. In the reaction pathway exploration, the transiency of MeOSO3- was disclosed, which was generated from esterification between the in situ generated HSO4- and MeOH, a rate-limiting step in the process. More importantly, the selectivity-controlling step was represented by the subsequent nucleophilic displacement between MeOSO3- and aldehydes. The ionic oxidant 1a ((NH4)2S2O8) with more N-H numbers in the cation, as compared with 1c ((n-Bu4N)2S2O8) and 1d ((PyH)2S2O8), has better performance in the oxidative esterification of aldehydes.

AB - A mild oxidative esterification of various aromatic aldehydes by sulfate radical redox system was presented. In the reaction pathway exploration, the transiency of MeOSO3- was disclosed, which was generated from esterification between the in situ generated HSO4- and MeOH, a rate-limiting step in the process. More importantly, the selectivity-controlling step was represented by the subsequent nucleophilic displacement between MeOSO3- and aldehydes. The ionic oxidant 1a ((NH4)2S2O8) with more N-H numbers in the cation, as compared with 1c ((n-Bu4N)2S2O8) and 1d ((PyH)2S2O8), has better performance in the oxidative esterification of aldehydes.

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Oxidation of Aromatic Aldehydes to Esters: A Sulfate Radical Redox System

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