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One-pot generation of benzynes from 2-aminophenylboronates via a Rh(ii)-catalyzed N–H amination/oxidation/elimination cascade process

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Abstract

This article describes the first application of 2-aminophenylboronates as precursors for benzynes. Utilizing Rh2(HNCOCF3)4 as the catalyst, Rh(II)-nitrene-mediated N–H amination of the starting material triggered a cascade of oxidation/elimination processes resulting in the generation of benzynes, thus providing suitable conditions for a one-pot cycloaddition with azides or furans. The transformation proceeded under acid-, base-, and fluoride-free conditions, below ambient temperature, and was applicable to a range of substrates containing glycoside and nucleoside moieties, as well as silyl-functional groups.

Graphical abstract: One-pot generation of benzynes from 2-aminophenylboronates via a Rh(ii)-catalyzed N–H amination/oxidation/elimination cascade process

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Publication details

The article was received on 09 Sep 2019, accepted on 04 Oct 2019 and first published on 18 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01115C
Org. Chem. Front., 2020, Advance Article
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    One-pot generation of benzynes from 2-aminophenylboronates via a Rh(II)-catalyzed N–H amination/oxidation/elimination cascade process

    M. Ito, A. Tanaka, K. Hatakeyama, E. Kano, K. Higuchi and S. Sugiyama, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01115C

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