Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization

Peng Ji, Cassondra C. Davies, Feng Gao, Jing Chen, Xiang Meng, Kendall N. Houk (), Shuming Chen () and Wei Wang ()
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Peng Ji: University of Arizona
Cassondra C. Davies: Oberlin College
Feng Gao: University of Arizona
Jing Chen: University of Arizona
Xiang Meng: University of Arizona
Kendall N. Houk: University of California
Shuming Chen: Oberlin College
Wei Wang: University of Arizona

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract Reactions that lead to destruction of aromatic ring systems often require harsh conditions and, thus, take place with poor selectivities. Selective partial dearomatization of fused arenes is even more challenging but can be a strategic approach to creating versatile, complex polycyclic frameworks. Herein we describe a general organophotoredox approach for the chemo- and regioselective dearomatization of structurally diverse polycyclic aromatics, including quinolines, isoquinolines, quinoxalines, naphthalenes, anthracenes and phenanthrenes. The success of the method for chemoselective oxidative rupture of aromatic moieties relies on precise manipulation of the electronic nature of the fused polycyclic arenes. Mechanistic studies show that the addition of a hydrogen atom transfer (HAT) agent helps favor the dearomatization pathway over the more thermodynamically downhill aromatization pathway. We show that this strategy can be applied to rapid synthesis of biologically valued targets and late-stage skeletal remodeling en route to complex structures.

Date: 2022
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32201-7

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DOI: 10.1038/s41467-022-32201-7

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