A multitasking functional group leads to structural diversity using designer C–H activation reaction cascades

Ying Chen, Dongqi Wang, Pingping Duan, Rong Ben, Lu Dai, Xiaoru Shao, Mei Hong, Jing Zhao () and Yong Huang ()
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Ying Chen: State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Institute of Chemistry and BioMedical Sciences, Nanjing University
Dongqi Wang: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Pingping Duan: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Rong Ben: State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Institute of Chemistry and BioMedical Sciences, Nanjing University
Lu Dai: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Xiaoru Shao: Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University
Mei Hong: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Jing Zhao: State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Institute of Chemistry and BioMedical Sciences, Nanjing University
Yong Huang: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School

Nature Communications, 2014, vol. 5, issue 1, 1-9

Abstract: Abstract The C–H activation strategy has become one of the preferred methods to introduce chemical functionality to a chemically inert carbon atom. Intensive efforts have been devoted to developing either versatile bond formations (product structural diversity) or effective directing groups (substrate site selectivity). From the views of medicinal and synthetic practitioners, the C–H activation approach remains inadequate due to its limitation to point-to-point derivatization. Direct assembly of 3D molecular complexity in a single step remains elusive for this strategy. Towards this goal, a multitasking functional group is required to accomplish several missions in one pot: site selecitivity, cleavability and redox versatility. We demonstrate that an oxyacetamide group is such a multifunctional warhead that enables a series of C–H functionalization cascades and allows direct access to structurally diverse polycyclic heterocyles in one pot. The progress of these reaction cascades were fully controlled by oxidants and temperature. The proliferation of the reaction chain can be extended to a four-step cascade.

Date: 2014
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DOI: 10.1038/ncomms5610

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