Synthesis of difluoromethylated allenes through trifunctionalization of 1,3-enynes

Munira Taj Muhammad, Yihang Jiao, Changqing Ye, Mong-Feng Chiou, Muhammad Israr, Xiaotao Zhu, Yajun Li, Zhenhai Wen, Armido Studer and Hongli Bao ()
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Munira Taj Muhammad: University of Chinese Academy of Sciences
Yihang Jiao: University of Chinese Academy of Sciences
Changqing Ye: University of Chinese Academy of Sciences
Mong-Feng Chiou: University of Chinese Academy of Sciences
Muhammad Israr: University of Chinese Academy of Sciences
Xiaotao Zhu: University of Chinese Academy of Sciences
Yajun Li: University of Chinese Academy of Sciences
Zhenhai Wen: University of Chinese Academy of Sciences
Armido Studer: Westfälische Wilhelms-Universität Corrensstraße 40
Hongli Bao: University of Chinese Academy of Sciences

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Organofluorine compounds have shown their great value in many aspects. Moreover, allenes are also a class of important compounds. Fluorinated or fluoroalkylated allenes might provide an option as candidates for drug and material developments, as allenes allow a great number of valuable transformations. Herein, we report a metal-free synthesis of difluoromethylated allenes via regioselective trifunctionalization of 1,3-enynes. This method proceeds through double C–F bond formation with concomitant introduction of an amino group to the allene. Synthetic applications are conducted and preliminary mechanistic studies suggest that a two-step pathway is involved. DFT calculations revealed an unusual dibenzenesulfonimide-assisted fluorination/fluoroamination with NFSI. In addition, kinetic reaction study revealed the induction period of both major and side products to support the proposed reaction mechanism. This work offers a convenient approach for the synthesis of a range of difluoromethylated allenes and is also a rare example of trifunctionalization of 1,3-enynes.

Date: 2020
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DOI: 10.1038/s41467-019-14254-3

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