Selectivity in the Aerobic Dearomatization of Phenols: Total Synthesis of Dehydronornuciferine by Chemo‐ and Regioselective Oxidation,Angewandte Chemie International Edition

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Selectivity in the Aerobic Dearomatization of Phenols: Total Synthesis of Dehydronornuciferine by Chemo‐ and Regioselective Oxidation
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-01-16 , DOI: 10.1002/anie.201710271
Kenneth Virgel N. Esguerra ₁ , Jean-Philip Lumb ₁

Affiliation

We describe a selective aerobic oxidation of meta‐biaryl phenols that enables rapid access to functionalized phenanthrenes. Aerobic oxidations attract interest due to their efficiency, but remain underutilized in complex molecule settings due to challenges of selectivity. We discuss these issues in the context of Cu catalysis, and highlight the advantages of confining oxygen activation and substrate oxidation to the catalyst's inner‐coordination sphere. This gives rise to predictable selectivity that we use for a concise synthesis of the aporphine dehydronornuciferine.

中文翻译：

苯酚需氧脱芳香化的选择性：通过化学和区域选择性氧化全合成脱氢核糖核酸

我们描述了间联芳基苯酚的选择性好氧氧化，该氧化使得能够快速访问官能化的菲。有氧氧化由于其效率而引起人们的关注，但由于选择性的挑战，在复杂的分子环境中仍未得到充分利用。我们在铜催化的背景下讨论了这些问题，并着重指出了将氧活化和底物氧化限制在催化剂的内配位球上的优势。这产生了可预测的选择性，我们将其用于简明合成的阿朴啡脱氢核糖核酸。

更新日期：2018-01-16

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