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Trifluoromethyl radical triggered radical cyclization of N-benzoyl ynamides leading to isoindolinones

Abstract

Under photocatalytic reductive conditions, trifluoromethyl radical addition onto an ynamide followed by cyclization on a benzoyl moiety produces diverse isoindolinone platforms with good yields. The selectivity of the radical cyclization, N-benzoyl vs. N-benzyl as radical acceptor and the E/Z ratio of isomers have been rationalized by modeling.

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Acknowledgements

We thank Sorbonne Université, CNRS and Servier for funding. The authors wish to acknowledge the analytical department of IDRS — Servier for the compounds analyses (IR, NMR, HR-MS) and the SRIMC department for the syntheses on big scale. This work was granted access to the high performance computing (HPC) resources of the HPCaVe Centre at Sorbonne Université and to the HPC resources of IDRIS under the allocation 2018-A0050810312 made by GENCI. The authors wish to acknowledge support from the ICMG Chemistry Nanobio Platform-PCECIC, Grenoble, for calculations facilities. Jérémy Forté is acknowledged for the X-ray diffraction analyses as well as Conor Dent Cullen and Scott Warchal for proofreading the manuscript.

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Correspondence to Cyril Ollivier or Louis Fensterbank.

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Cassé, M., Nisole, C., Dossmann, H. et al. Trifluoromethyl radical triggered radical cyclization of N-benzoyl ynamides leading to isoindolinones. Sci. China Chem. 62, 1542–1546 (2019). https://doi.org/10.1007/s11426-019-9627-x

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Keywords

  • ynamides
  • trifluoromethylation
  • photocatalysis
  • cascade reactions
  • tandem processes
  • isoindolinones
  • modeling