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Clean protocol for deoxygenation of epoxides to alkenes via catalytic hydrogenation using gold

机译：清洁协议环氧化合物的脱氧作用通过催化烯烃加氢使用黄金

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摘要

The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)(3) is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts.
机译：烯烃的环氧化反应作为一个策略来保护碳碳双键是众所周知的在有机合成过程逆反应,去/脱氧环氧化合物欠发达得多,尽管它合成的潜在效用取代烯烃。协议的选择去环氧化合物,通过结合商用有机磷配体和金纳米粒子(非盟NP)。环氧化合物的脱氧,发现催化系统也使选择性减少N-oxides并使用分子亚砜氢气作为还原剂。结合triethylphosphite P(诗人)(3)明显比只盟NPs活性。不仅是一种互补Au-catalyzed方法还原反应在温和的条件下,但是也为选择一个有效的过程减少各种有价值的分子这将是综合不方便甚至难以访问的选择合成协议或通过使用经典过渡金属催化剂。

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