Palladium-catalyzed allene synthesis enabled by β-hydrogen elimination from sp2-carbon

Ge Zhang, Yi-Kang Song, Fang Zhang, Ze-Jian Xue, Meng-Yao Li, Gui-Shan Zhang, Bin-Bin Zhu, Jing Wei (), Chunsen Li, Chen-Guo Feng () and Guo-Qiang Lin ()
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Ge Zhang: Shanghai University of Traditional Chinese Medicine
Yi-Kang Song: Shanghai University of Traditional Chinese Medicine
Fang Zhang: Shanghai University of Traditional Chinese Medicine
Ze-Jian Xue: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Meng-Yao Li: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Gui-Shan Zhang: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Bin-Bin Zhu: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Jing Wei: State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
Chunsen Li: State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
Chen-Guo Feng: Shanghai University of Traditional Chinese Medicine
Guo-Qiang Lin: Shanghai University of Traditional Chinese Medicine

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract The rational design based on a deep understanding of the present reaction mechanism is an important, viable approach to discover new organic transformations. β-Hydrogen elimination from palladium complexes is a fundamental reaction in palladium catalysis. Normally, the eliminated β-hydrogen has to be attached to a sp3-carbon. We envision that the hydrogen elimination from sp2-carbon is possible by using thoroughly designed reaction systems, which may offer a new strategy for the preparation of allenes. Here, we describe a palladium-catalyzed cross-coupling of 2,2-diarylvinyl bromides and diazo compounds, where a β-vinylic hydrogen elimination from allylic palladium intermediate is proposed to be the key step. Both aryl diazo carbonyl compounds and N-tosylhydrazones are competent carbene precursors in this reaction. The reaction mechanism is explored by control experiments, KIE studies and DFT calculations.

Date: 2021
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DOI: 10.1038/s41467-020-20740-w

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