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.
Cyclic Diaryl λ3-Bromanes as Original Aryne Precursors / Lanzi, M.; Dherbassy, Q.; Wencel-Delord, J.. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - 60:27(2021), pp. 14852-14857. [10.1002/anie.202103625]
Cyclic Diaryl λ3-Bromanes as Original Aryne Precursors
Lanzi M.;
2021-01-01
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
