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Cyclic Diaryl λ 3 ‐Bromanes as Original Aryne Precursors
Author(s) -
Lanzi Matteo,
Dherbassy Quentin,
WencelDelord Joanna
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202103625
Subject(s) - aryne , hypervalent molecule , reactivity (psychology) , chemistry , base (topology) , combinatorial chemistry , computational chemistry , medicinal chemistry , organic chemistry , mathematics , reagent , medicine , mathematical analysis , alternative medicine , pathology
Despite the widespread application of hypervalent iodines, the corresponding λ 3 ‐bromanes are less explored. Herein we report a general, safe, and high‐yielding strategy to access cyclic diaryl λ 3 ‐bromanes. These unique compounds feature reactivity that is appealing and complementary to that of λ 3 ‐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.