Visible Light Photocatalytic Reduction of O-Thiocarbamates: Development of a Tin-Free Barton-McCombie Deoxygenation Reaction
Visible Light Photocatalytic Reduction of O-Thiocarbamates: Development of a Tin-Free Barton-McCombie Deoxygenation Reaction
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DOI：
10.1002/adsc.201400729
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发表时间：
2014-09-15
影响因子：
5.4
通讯作者：
Ollivier, Cyril
中科院分区：
文献类型：
--
作者：
Chenneberg, Ludwig;Baralle, Alexandre;Ollivier, Cyril
Barton-McCombie脱氧反应是有机化学家工具箱中最重要的反应之一，也是许多方法学发展的主题。在这项研究中，我们报告了一个光催化氧化还原脱氧仲和叔醇从硫代氨基甲酸酯前体在可见光活化。在Hunig碱作电子给体的条件下，铱配合物Ir（ppy）（3）是最有效的催化剂。基于荧光猝灭实验和循环伏安法对机理进行了研究。
The Barton-McCombie deoxygenation is one of the most important transformations in the toolbox of organic chemists which has been the subject of a number of methodological developments. In this study, we report a photocatalyzed redox deoxygenation of secondary and tertiary alcohols from thiocarbamate precursors under visible light activation. The iridium complex Ir(ppy)(3) proved to be the most efficient catalyst in the presence of Hunig's base as sacrifial electron donor. A mechanistic investigation is presented based on fluorescence quenching experiments and cyclic voltammetry.