Selectivity in the photo-Fenton and photocatalytic hydroxylation of biphenyl-4-carboxylic acid and derivatives (viz. 4-phenylsalicylic acid and 5-phenylsalicylic acid)

Hathway T.; Chernyshov D.L.; Jenks W.S.

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Selectivity in the photo-Fenton and photocatalytic hydroxylation of biphenyl-4-carboxylic acid and derivatives (viz. 4-phenylsalicylic acid and 5-phenylsalicylic acid)

机译：联苯-4-羧酸及其衍生物（即4-苯基水杨酸和5-苯基水杨酸）的光芬顿选择性和光催化羟基化反应

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The selectivity of hydroxylation of the distal rings of 4-phenylbenzoic acid, 4-phenylsalicylic acid, and 5-phenylsalicylic acid were determined using partial TiO_2-mediated photocatalytic degradation and photo-Fenton conditions. This separation of the binding site from the phenyl group being hydroxylated allows a less-biased evaluation. The hydroxylation regiochemistry behaves as qualitatively expected for an electrophilic reaction, given the assumption that 4-carboxyphenyl is a slightly electron-withdrawing substituent. Selectivity for hydroxylation of the distal phenyl in 4- and 5-phenylsalicylic acid is reversed, due to the reversal of the electronic demand, while adsorption to the TiO_2 surface is assumed to be analogous for the two structures.

机译：使用部分TiO_2介导的光催化降解和光芬顿条件，确定了4-苯基苯甲酸，4-苯基水杨酸和5-苯基水杨酸的远端羟基的选择性。结合位点与被羟基化的苯基的这种分离允许偏斜的评估。假设4-羧基苯基是一个轻度吸电子的取代基，则羟基化区域化学反应的性质如亲电反应所预期。由于电子需求的逆转，使4-和5-苯基水杨酸中的远端苯基羟基化的选择性相反，而对于这两种结构，假定对TiO_2表面的吸附是相似的。

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《Journal of Physical Organic Chemistry》 |2011年第12期|共6页
作者
Hathway T.; Chernyshov D.L.; Jenks W.S.;
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正文语种 eng
中图分类有机化学一般性问题;
关键词
hydroxylation; photo-Fenton; photocatalysis; selectivity; titanium dioxide;

机译：羟基化;光芬顿;光催化;选择性;二氧化钛;

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1. Selectivity in the photo-Fenton and photocatalytic hydroxylation of biphenyl-4-carboxylic acid and derivatives (viz. 4-phenylsalicylic acid and 5-phenylsalicylic acid) [J] . Hathway T., Chernyshov D.L., Jenks W.S. Journal of Physical Organic Chemistry . 2011,第12期

机译：联苯-4-羧酸及其衍生物（即4-苯基水杨酸和5-苯基水杨酸）的光芬顿选择性和光催化羟基化反应
2. Ruthenium-Catalyzed C-H Hydroxylation in Aqueous Acid Enables Selective Functionalization of Amine Derivatives [J] . Mack James B.C., Gipson John D., Du Bois Justin, Journal of the American Chemical Society . 2017,第28期

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Selectivity in the photo-Fenton and photocatalytic hydroxylation of biphenyl-4-carboxylic acid and derivatives (viz. 4-phenylsalicylic acid and 5-phenylsalicylic acid)

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