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. 2021 Jun 25;60(27):14852-14857.
doi: 10.1002/anie.202103625. Epub 2021 May 26.

Cyclic Diaryl λ3 -Bromanes as Original Aryne Precursors

Matteo Lanzi  1 , Quentin Dherbassy  1 , Joanna Wencel-Delord  1
Affiliations

Cyclic Diaryl λ3 -Bromanes as Original Aryne Precursors

Matteo Lanzi et al. Angew Chem Int Ed Engl. .

Abstract

Despite the widespread application of hypervalent iodines, the corresponding λ3 -bromanes are less explored. Herein we report a general, safe, and high-yielding strategy to access cyclic diaryl λ3 -bromanes. These unique compounds feature reactivity that is appealing and complementary to that of λ3 -iodanes, generating arynes under mild reaction conditions and in the presence of a weak base. Accordingly, formal meta-selective transition-metal-free C-O and C-N couplings may be achieved. Mechanistic studies unambiguously support the aryne generation mechanism.

Keywords: arynes; hypervalent bromine; hypervalent iodine; metal-free coupling; λ3-bromanes.

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References

    1. None
    1. Encyclopedia of Inorganic Chemistry, Wiley, Hoboken, 2006;
    1. M. Ochiai in Chemistry of Hypervalent Compounds (Ed.: K. Akiba), Wiley-VCH, New York, 1999, chap. 12.
    1. None
    1. A. Yoshimura, V. V. Zhdankin, Chem. Rev. 2016, 116, 3328-3435;

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