Abstract
Rh(ii)-Nitrene-mediated N–H amination of 2-aminophenylboronates triggered a cascade of oxidation/elimination processes resulting in the generation of benzynes.
Highlights
Benzynes are unique reactive intermediates that participate in the simultaneous creation of two bonds, including C–C, C–H, or C–X (X = heteroatom) bonds, on adjacent aromatic carbons via a cycloaddition reaction or the sequential addition of a nucleophile and an electrophile.[1]
With a view to further enhancing the synthetic utility of these reactive species, significant efforts have been devoted to developing efficient benzyne precursors.[2,3,4,5,6]
As part of the research on the transformation of anilines using the Rh(II)-nitrene species,[7,8] we recently reported the catalytic single-step synthesis of N-aryl-N′-tosyldiazenes from primary anilines.8a In the presence of dirhodium(II) complexes as the catalysts and 2 equiv. of-2,4,6-trimethylphenyliodinane (TsNvIMes), anilines underwent N–H amination by Rh(II)-nitrene followed by oxidation to provide the products in one pot (Scheme 1a)
Summary
Of (tosylimino)-2,4,6-trimethylphenyliodinane (TsNvIMes), anilines underwent N–H amination by Rh(II)-nitrene followed by oxidation to provide the products in one pot (Scheme 1a). (b) Utilization of 2-aminophenylboronates as benzyne precursors through a Rh(II)-catalyzed N–H amination/oxidation/elimination cascade process. We report the utilization of 2-aminophenylboronates as novel benzyne precursors through the combined use of Rh2(HNCOCF3)[4] and TsNvIMes (Scheme 1b).
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