Benzene construction via organocatalytic formal [3+3] cycloaddition reaction

Tingshun Zhu, Pengcheng Zheng, Chengli Mou, Song Yang, Bao-An Song () and Yonggui Robin Chi ()
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Tingshun Zhu: School of Physical & Mathematical Sciences, Nanyang Technological University
Pengcheng Zheng: School of Physical & Mathematical Sciences, Nanyang Technological University
Chengli Mou: School of Physical & Mathematical Sciences, Nanyang Technological University
Song Yang: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University
Bao-An Song: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University
Yonggui Robin Chi: School of Physical & Mathematical Sciences, Nanyang Technological University

Nature Communications, 2014, vol. 5, issue 1, 1-6

Abstract: Abstract The benzene unit, in its substituted forms, is a most common scaffold in natural products, bioactive molecules and polymer materials. Nearly 80% of the 200 best selling small molecule drugs contain at least one benzene moiety. Not surprisingly, the synthesis of substituted benzenes receives constant attentions. At present, the dominant methods use pre-existing benzene framework to install substituents by using conventional functional group manipulations or transition metal-catalyzed carbon-hydrogen bond activations. These otherwise impressive approaches require multiple synthetic steps and are ineffective from both economic and environmental perspectives. Here we report an efficient method for the synthesis of substituted benzene molecules. Instead of relying on pre-existing aromatic rings, here we construct the benzene core through a carbene-catalyzed formal [3+3] reaction. Given the simplicity and high efficiency, we expect this strategy to be of wide use especially for large scale preparation of biomedicals and functional materials.

Date: 2014
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DOI: 10.1038/ncomms6027

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