化学
二羟基化
环加成
组合化学
有机化学
生化工程
纳米技术
对映选择合成
催化作用
工程类
材料科学
作者
Emma H. Southgate,Jola Pospech,Junkai Fu,Daniel R. Holycross,David Šarlah
出处
期刊:Nature Chemistry
[Springer Nature]
日期:2016-08-22
卷期号:8 (10): 922-928
被引量:146
摘要
Aromatic hydrocarbons are some of the most elementary feedstock chemicals, produced annually on a million metric ton scale, and are used in the production of polymers, paints, agrochemicals and pharmaceuticals. Dearomatization reactions convert simple, readily available arenes into more complex molecules with broader potential utility, however, despite substantial progress and achievements in this field, there are relatively few methods for the dearomatization of simple arenes that also selectively introduce functionality. Here we describe a new dearomatization process that involves visible-light activation of small heteroatom-containing organic molecules-arenophiles-that results in their para-cycloaddition with a variety of aromatic compounds. The approach uses N-N-arenophiles to enable dearomative dihydroxylation and diaminodihydroxylation of simple arenes. This strategy provides direct and selective access to highly functionalized cyclohexenes and cyclohexadienes and is orthogonal to existing chemical and biological dearomatization processes. Finally, we demonstrate the synthetic utility of this strategy with the concise synthesis of several biologically active compounds and natural products.
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