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. 2024 Mar 25;30(18):e202303953.
doi: 10.1002/chem.202303953. Epub 2024 Feb 7.

Sterically Congested Protecting Group for a Boronyl Group in Iterative Aminations

Takaki Nojiri  1 , Naoki Tsuchiya  1 , Takashi Nishikata  1
Affiliations

Sterically Congested Protecting Group for a Boronyl Group in Iterative Aminations

Takaki Nojiri et al. Chemistry. .

Abstract

In this study, we found that the sterically bulky α-hydroxycarboxamide moiety is a suitable framework for protecting the boronyl group of boron reagents during aminations. Condensation of α-hydroxycarboxamide with ArB(OH)2 produced aryloxazaborolidinone (ArOxB). The reactivity of the C-B bond in ArOxB is easily controlled by the steric and weak electronic effects of the backbone. H2N-(or Br-)ArOxB underwent Chan-Evans-Lam (C-E-L) or Buchwald-Hartwig (B-H) amination with retaining the C-B bond. On the other hand, direct C-E-L amination of ArOxB was also possible in an oxidative atmosphere, in which the C-B bond was activated by CuII species. Our methodology is effective for the precise synthesis of two or more arylamino group substituted arenes.

Keywords: Amination; Boron compound; Oxazaborolidinone; Protecting.

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References

    1. Y. Baqi, C. E. Müller, Nat. Protoc. 2010, 5, 945–953.
    1. B. J. Deadman, M. D. Hopkin, I. R. Baxendale, S. V. Ley, Org. Biomol. Chem. 2013, 11, 1766–1800.
    1. G. Bertuzzi, E. Locatelli, D. Colecchia, P. Calandro, B. F. Bonini, J. Z. Chandanshive, A. Mazzanti, P. Zani, M. Chiariello, M. Comes Franchini, Eur. J. Med. Chem. 2016, 117, 1–7.
    1. None
    1. E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2007, 129, 6716–6717;

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