Arenophile-Mediated Dearomative Reduction

Mikiko Okumura; Stephanie M Nakamata Huynh; Jola Pospech; David Sarlah

doi:10.1002/anie.201609686

Arenophile-Mediated Dearomative Reduction

Angew Chem Int Ed Engl. 2016 Dec 19;55(51):15910-15914. doi: 10.1002/anie.201609686. Epub 2016 Nov 23.

Authors

Mikiko Okumura¹, Stephanie M Nakamata Huynh¹, Jola Pospech¹, David Sarlah¹

Affiliation

¹ Roger Adams Laboratory, Department of Chemistry, University of Illinois, Illinois, 61801, USA.

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.

Keywords: arenes; arenophiles; dearomatization; functionalization; photochemistry.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Grants and funding

R01 GM122891/GM/NIGMS NIH HHS/United States