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Arenophile‐Mediated Dearomative Reduction
Author(s) -
Okumura Mikiko,
Nakamata Huynh Stephanie M.,
Pospech Jola,
Sarlah David
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201609686
Subject(s) - derivatization , moiety , cycloaddition , chemistry , combinatorial chemistry , fragmentation (computing) , surface modification , reduction (mathematics) , diimide , stereochemistry , organic chemistry , computer science , molecule , mathematics , catalysis , perylene , high performance liquid chromatography , geometry , operating system
A dearomative reduction of simple arenes has been developed which employs a visible‐light‐mediated cycloaddition of arenes with an N‐N‐arenophile and in situ diimide reduction. Subsequent cycloreversion or fragmentation of the arenophile moiety affords 1,3‐cyclohexadienes or 1,4‐diaminocyclohex‐2‐enes, compounds that are not synthetically accessible using existing dearomatization reactions. Importantly, this strategy also provides numerous opportunities for further derivatization as well as site‐selective functionalization of polynuclear arenes.