PhSeBr mediated hydroxylative oxidative dearomatization of naphthols - an open air facile one-pot synthesis of ketols

Sarkar Debayan; Ghosh Manoj Kumar; Rout Nilendri; Giri Santanab

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PhSeBr mediated hydroxylative oxidative dearomatization of naphthols - an open air facile one-pot synthesis of ketols

机译：phsebr介导萘酚的羟基氧化脂肪化 - 一个露天容易的酮一罐合成酮

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A new methodology for oxidative-dearomatization of planar phenols is described. An economic, viable one-pot metal free protocol for direct conversion of naphthols to a-ketols is reported. Naphthols were found to undergo facile unprecedented oxidative dearomatization with regioselective hydroxylation with phenyl selenyl bromide in open air conditions. Quaternary stereocenters were developed along with formation of sterically demanding a-and g-ketols with high yields. Functional group tolerance like esters is revealed. A thorough study of the stereoelectronic demands of the unusual oxy-selenium reactive intermediate involved in dearomatization of 1- and 2-naphthols is carried out. 4-Hydroxy cyclohexadieneone and cyclohexadieneone aryl ethers were generated from dialkyl-phenols under similar reaction conditions providing direct evidence of the mechanical postulate. The first instance of the phenoxy-selenium interaction leading to facile dearomatization of arenes is highlighted in this manuscript.

机译：描述了一种新的氧化 - 苯酚的氧化方法方法。据报道了一种用于直接转化萘酚对A-Ketols的一种经济，可行的一罐金属的无运动方案。发现萘酚与戊基硒溴化物在露天空气条件下与苯基硒溴化物的区域选择性羟基化进行了脱位的前所未有的氧化脂肪化。开发了季度立体封闭者以及形成具有高产率高的空间苛刻的A-和G-Ketol。透露酯的功能组耐受性。进行了对涉及1-和2-萘酚的异常氧化硒反应性中间体的立体电子需求的彻底研究。在类似的反应条件下，从二烷基酚类产生4-羟基环己二烯酮和环己二烯酮芳基醚。提供机械假设的直接证据。在本手稿中突出了苯氧硒相互作用的第一个苯氧硒相互作用的实例，其突出了阶段。

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《RSC Advances》 |2016年第32期|共9页
作者
Sarkar Debayan; Ghosh Manoj Kumar; Rout Nilendri; Giri Santanab;
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Natl Inst Technol Organ Synth &

Mol Engn Lab Dept Chem Rourkela 769008 Odisha India;

Natl Inst Technol Organ Synth &

Mol Engn Lab Dept Chem Rourkela 769008 Odisha India;

Natl Inst Technol Organ Synth &

Mol Engn Lab Dept Chem Rourkela 769008 Odisha India;

Natl Inst Technol Theoret Chem Lab Dept Chem Rourkela 769008 Odisha India;

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正文语种 eng
中图分类化学;
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1. PhSeBr mediated hydroxylative oxidative dearomatization of naphthols - an open air facile one-pot synthesis of ketols [J] . Sarkar Debayan, Ghosh Manoj Kumar, Rout Nilendri, RSC Advances . 2016,第32期

机译：phsebr介导萘酚的羟基氧化脂肪化 - 一个露天容易的酮一罐合成酮
2. Phase-Transfer-Catalyzed Oxaziridine-Mediated Hydroxylative Phenol and Naphthol Dearomatization [J] . Grandclaudon Charlotte, Toullec Patrick Y. European journal of organic chemistry . 2016,第2期

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3. Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives [J] . Yu Zhang, Yuting Liao, Xiaohua Liu, Chemical science . 2017,第9期

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机译：ULVA Fasciata介导的氧化锌纳米晶的氧化锌纳米晶的制备6-氨基-3-甲基-4-苯基-2,4-二氢吡喃-5-碳腈合成2,3-C吡唑-5-腈
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机译：杂环合成的新进展及其在绿色化学中的应用。 I.使用相转移催化剂（Aliquat-336）简单且基本上一锅合成N-胺化的杂环。二。药学上重要的吡咯衍生物的合成。三，在绿色化学中的应用：在无溶剂的中性条件下，表面活性剂介导的环境友好的芳族酯裂解和酯交换反应。
6. Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives [O] . Yu Zhang, Yuting Liao, Xiaohua Liu, 2017

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7. Oxidative dearomatization of naphthols –a novel synthesis of sulphoxide templates [O] . Sahoo S R 2014

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8. One-Pot Synthesis of Aromatic Methyl Esters by Electrochemical Oxidation ofAldehydes Mediated by Biscoenzyme Catalysis [R] . Tam, S. W., Jimenez, L., Diederich, F. 1992

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PhSeBr mediated hydroxylative oxidative dearomatization of naphthols - an open air facile one-pot synthesis of ketols

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