An unprecedented deoxygenation protocol of benzylic alcohols using bis(1-benzotriazolyl)-methanethione

Kumar Dhananjay; Singh Anoop S.; Tiwari Vinod K.

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An unprecedented deoxygenation protocol of benzylic alcohols using bis(1-benzotriazolyl)-methanethione

机译：使用双（1-苯并三唑基） - 甲基硫乙基乙基醇的前所未有的脱氧方案

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A facile and regioselective two-step protocol for the deoxygenation of benzylic alcohols using bis(benzotriazole) methanethione has been devised. Benzotriazole derivatives, namely, benzyloxythioacylbenzotriazoles (ROCSBt), on reaction with silanes or Bu3SnH under microwave irradiation or conventional heating undergo a free radical beta-scission of C-O bond instead of N-N bond (benzotriazole ring cleavage) to afford a deoxy product. The methodology has various applications because it selectively deoxygenates benzylic alcohols with the aid of a relatively nontoxic (TMS)(3)SiH reagent as an acceptable alternate to Bu3SnH.

机译：已经设计了使用双（苯并三唑）甲基硫乙酮的苄醇的脱氧的容易和区域的两步方案。苯并三唑衍生物，即苄氧基硫代苯基苯并三唑（ROCSBT），在微波辐射或常规加热下与硅烷或BU3SH的反应经历自由基β-Sc-S键，代替N-N键（苯并三唑环裂解），得到脱氧产物。该方法具有各种应用，因为借助于相对无毒性（3）SiH试剂，选择性地脱氧邻氧醇作为与Bu3snH的可接受的交替。

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《RSC Advances》 |2015年第40期|共10页
作者
Kumar Dhananjay; Singh Anoop S.; Tiwari Vinod K.;
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Banaras Hindu Univ Fac Sci Dept Chem Varanasi 221005 Uttar Pradesh India;

Banaras Hindu Univ Fac Sci Dept Chem Varanasi 221005 Uttar Pradesh India;

Banaras Hindu Univ Fac Sci Dept Chem Varanasi 221005 Uttar Pradesh India;

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1. An unprecedented deoxygenation protocol of benzylic alcohols using bis(1-benzotriazolyl)-methanethione [J] . Kumar Dhananjay, Singh Anoop S., Tiwari Vinod K. RSC Advances . 2015,第40期

机译：使用双（1-苯并三唑基） - 甲基硫乙基乙基醇的前所未有的脱氧方案
2. Microreactor mediated deoxygenation of benzylic alcohols in a biphasic organic-aqueous medium [J] . Seo Seung Woo, Song Hyun Seung, Song Ju Ha, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2015,第21期

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3. Deoxygenation of tertiary and secondary benzylic alcohols into alkanes with triethylsilane catalyzed by solid acid tin(IV) ion-exchanged montmorillonite [J] . Tandiary Michael Andreas, Masui Yoichi, Onaka Makoto Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2014,第30期

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4. Aerobic Oxidation of Benzylic Alcohols Catalyzed by Palladium-Bisoxazoline Monolayer on Single Crystal Silicon Surface [C] . Kenji Hara, Shinobu Tayama, Hidekazu Kano, Symposium on Organometallic Chemistry . 2004

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6. Unprecedented deoxygenation at C-7 of the ansamitocin core during mutasynthetic biotransformations [O] . Tobias Knobloch, Gerald Dräger, Wera Collisi, 2012

机译：突变合成生物转化过程中安那霉素核心C-7处前所未有的脱氧
7. Oxidation of benzylic and some aliphatic alcohols 1,2-ethylenebis(triphenylphosphonium)chlorochromate (EBTPPCC): As a new, an efficient and mild oxidant [O] . M. Gholizadeh, M. Ebrahimpour, S.F. Hojati, 2014

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An unprecedented deoxygenation protocol of benzylic alcohols using bis(1-benzotriazolyl)-methanethione

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