Radical Cation Diels‐Alder Reactions of Non‐Conjugated Alkenes as Dienophiles by Electrocatalysis1. Issue 6 (15th April 2019)

• Record Type: Journal Article
• Authors: Ozaki, Atsushi; Yamaguchi, Yusuke; Okada, Yohei; Chiba, Kazuhiro
• Is Part Of: Chinese journal of chemistry. Volume 37:Issue 6(2019)
• Page Start: 561
• Page End: 564
• Publication Date: 2019-04-15
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.201900054
• Languages: English
• ISSNs: 1001-604X

Abstract

Summary of main observation and conclusion: 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. Abstract : 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.