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Arenophile-Mediated Dearomative Reduction.

ABSTRACT: 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.

SUBMITTER: Okumura M

PROVIDER: S-EPMC6043355 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Arenophile-Mediated Dearomative Reduction.

Okumura Mikiko M Nakamata Huynh Stephanie M SM Pospech Jola J Sarlah David D

Angewandte Chemie (International ed. in English) 20161123 51

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 ...[more]

PMID: 27879027

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