Radical Cation Diels‐Alder Reactions of Non‐Conjugated Alkenes as Dienophiles by Electrocatalysis,Chinese Journal of Chemistry

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Radical Cation Diels‐Alder Reactions of Non‐Conjugated Alkenes as Dienophiles by Electrocatalysis
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2019-04-15 , DOI: 10.1002/cjoc.201900054
Atsushi Ozaki ₁ , Yusuke Yamaguchi ₁ , Yohei Okada ₂ , Kazuhiro Chiba ₁

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Radical cation Diels‐Alder reactions provide a powerful method for the construction of six‐membered ring systems between both electron‐rich dienes and dienophiles. However, the most recent examples of this class have been limited to β‐methylstyrenes as dienophiles; the use of non‐conjugated alkenes remains challenging. The present study describes the serendipitous development of novel radical cation Diels‐Alder reactions by electrocatalysis that use non‐conjugated alkenes as dienophiles. The key to successful transformation involves highly substituted cyclohexenyl radical cations that are stable enough to be reduced by intermolecular single electron transfer.

中文翻译：

非共轭烯烃作为亲二烯体的自由基阳离子Diels-Alder反应的电催化

自由基阳离子Diels-Alder反应提供了一种在富电子二烯和亲二烯体之间构建六元环系统的有力方法。然而，此类的最新例子仅限于β-甲基苯乙烯作为亲二烯体。非共轭烯烃的使用仍然具有挑战性。本研究描述了使用非共轭烯烃作为亲二烯体的电催化新自由基Diels-Alder反应的偶然发展。成功转化的关键涉及高度取代的环己烯基自由基阳离子，该阳离子足够稳定，可以被分子间单电子转移还原。

更新日期：2019-04-15

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