Direct β-Alkylation of Aldehydes via Photoredox Organocatalysis,Journal of the American Chemical Society

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Direct β-Alkylation of Aldehydes via Photoredox Organocatalysis
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2014-04-29 , DOI: 10.1021/ja502639e
Jack A Terrett ₁ , Michael D Clift , David W C MacMillan

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Direct β-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated β-enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce β-alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C–H functionalization protocol can be achieved both inter- and intramolecularly. Mechanistic studies by various spectroscopic methods suggest that a reductive quenching pathway is operable.

中文翻译：

通过光氧化还原有机催化对醛进行直接 β-烷基化

通过光氧化还原催化和有机催化的协同结合，实现了饱和醛的直接β-烷基化。光子诱导的烯胺氧化提供了一种活化的β-烯胺基自由基中间体，它很容易与各种迈克尔受体结合，以高效的方式产生β-烷基醛。此外，这种氧化还原中性、原子经济的C-H官能化方案可以在分子间和分子内实现。通过各种光谱方法进行的机理研究表明，还原猝灭途径是可行的。

更新日期：2014-04-29

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