中文标题:无过渡金属高化学选择性和立体选择性的Se/DMF/H2O还原体系
英文标题:Transition-Metal-Free Highly Chemoselective and Stereoselective Reduction with Se/DMF/H2O System
刊物名称:Organic Letters, 2018, 20 (18), pp 5573–5577
作者姓名:李鸿辰、安翠、吴戈、李国兴、黄小波、高文霞、丁金昌、周云兵、刘妙昌、吴华悦
Abstract: A novel metal-free reduction system, in which H2Se (or HSe-) produced in situ from Se/DMF/H2O acts as the active reducing species, has been developed. By using water as an inexpensive, safe, and environmentally friendly surrogate as the hydrogen donor, this new reduction system incorporating Se/DMF/H2O displayed high selectivity and good activity in the reduction of α,β-unsaturated ketones and alkynes. Therefore, this reduction system has great potential to be a general and practical reduction methodology in organic transformation
研究现状:
选择性还原是合成天然产物,药物以及工业化学品最重要的方法之一,在过去的几十年里,我们以往通常致力于发展过渡金属催化还原体系;一系列基于钯、钌、铑、铱等过渡金属催化的还原体系被用于选择性还原α,β-不饱和羰基化合物为饱和的羰基化合物。然而,这些过渡金属催化体系通常会受成本高,产生有毒物质和难分离的影响,这限制了某种程度上在药物合成以及在工业的应用。从经济和环保的观点,使用无金属体系还原更有深远的意义。
创新点:
1、发现并且研究一种新型高效的无金属还原体系,在Se/DMF/H2O体系下实现多种类型底物的选择性还原;
2、选择廉价的水作为氢源,简单易得,对环境污染影响小;
3、官能团容忍性和底物普适性好;
4、可以通过D2O为氘源,合成氘代饱和羰基化合物以及氘代反式二芳基乙烯类化合物;
5、通过Se/DMF/H2O体系实现芳基醚化合物的脱甲基反应。
原文链接://doi.org/10.1021/acs.orglett.8b02244