期刊
NATURE COMMUNICATIONS
卷 13, 期 1, 页码 -出版社
NATURE PORTFOLIO
DOI: 10.1038/s41467-022-32201-7
关键词
-
资金
- NIH [5R01GM125920]
- University of Arizona
- NSF MRI [1920234]
- Oberlin College
- National Science Foundation [CHE1764328]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1920234] Funding Source: National Science Foundation
The synthesis of polycyclic structures bearing partially saturated (hetero)arenes is important. The authors develop a one-step method for selective dearomative functionalization of feedstock (hetero)arenes via organophotocatalysis. The method allows for rapid synthesis of biologically valued targets and late-stage skeletal remodeling en route to complex structures.
The synthesis of polycyclic structures bearing partially saturated (hetero)arenes is important as many of these structures have biological relevance. Here the authors develop a one-step method for selective dearomative functionalization of feedstock (hetero)arenes via organophotocatalysis. 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.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据