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Radical Cation Diels‐Alder Reactions of Non‐Conjugated Alkenes as Dienophiles by Electrocatalysis
Author(s) -
Ozaki Atsushi,
Yamaguchi Yusuke,
Okada Yohei,
Chiba Kazuhiro
Publication year - 2019
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900054
Subject(s) - chemistry , conjugated system , intermolecular force , ring (chemistry) , electrocatalyst , radical ion , electron transfer , combinatorial chemistry , organic chemistry , polymer , electrochemistry , molecule , ion , electrode
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.