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以酰基氨基硫代甲酸酯为自由基前体的苄醇的光催化氧化还原中性和还原脱氧烷基化反应

Photocatalytic Redox-Neutral and Reductive Deoxygenative Alkylation of Benzyl Alcohols Using -Acyl Carbamothioates as Radical Precursors.

作者信息

Li Junhao, Liu Yuanxin, Wang Li, Liu Yaqun, Chen Min

机构信息

Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070, China.

出版信息

J Org Chem. 2025 Mar 7;90(9):3308-3321. doi: 10.1021/acs.joc.4c02942. Epub 2025 Feb 26.

Abstract

Herein, we report a photocatalytic redox-neutral and reductive deoxygenative alkylation of -acyl carbamothioates from benzylic alcohols, with substituted Hantzsch esters and allylic sulfones to afford unsymmetrical 1,2-diaryl ethanes and allylarylmethanes, respectively. This protocol facilitates facile deoxyalkylation of primary, secondary, and tertiary benzylic alcohol-derived -acyl carbamothioates, which features mild reaction conditions, broad functional group tolerance, and the obviation of external S/O trapping reagents as well as transition metal-coupling catalysts.

摘要

在此,我们报道了一种光催化氧化还原中性且还原脱氧的烷基化反应,该反应利用苄醇、取代的汉斯酯和烯丙基砜对酰基氨基硫代甲酸酯进行反应,分别得到不对称的1,2 - 二芳基乙烷和烯丙基芳基甲烷。该方法促进了伯、仲和叔苄醇衍生的酰基氨基硫代甲酸酯的脱氧烷基化反应,具有反应条件温和、官能团耐受性广、无需外部硫/氧捕获试剂以及过渡金属偶联催化剂等特点。

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