Journal
NATURE CHEMISTRY
Volume 11, Issue 1, Pages 71-77Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/s41557-018-0156-y
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Funding
- National Basic Research Program of China (973 Program) [2015CB856600]
- National Natural Science Foundation of China [21632001, 21772002]
- Peking University Health Science Center [BMU20160541]
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Anilines are fundamental motifs in various chemical contexts, and are widely used in the industrial production of fine chemicals, polymers, agrochemicals and pharmaceuticals. A recent development for the synthesis of anilines uses the primary amination of C-H bonds in electron-rich arenes. However, there are limitations to this strategy: the amination of electron-deficient arenes remains a challenging task and the amination of electron-rich arenes has a limited control over regioselectivity-the formation of meta-aminated products is especially difficult. Here we report a site-directed C-C bond primary amination of simple and readily available alkylarenes or benzyl alcohols for the direct and efficient preparation of anilines. This chemistry involves a novel C-C bond transformation and offers a versatile protocol for the synthesis of substituted anilines. The use of O-2 as an environmentally benign oxidant is demonstrated, and studies on model compounds suggest that this method may also be used for the depolymerization of lignin.
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