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DOI: 10.1055/s-0039-1690893
Reductive Amination of Aryl Boronic Acids: Parallelism of the Catalytic Reactivity of Transition Metals and Main Group Elements in the C(sp2)–N Bond-Forming Reactions
This work was supported by the Russian Science Foundation (Project number 19-13-00094).Publication History
Received: 27 February 2020
Accepted after revision: 24 March 2020
Publication Date:
20 April 2020 (online)
Abstract
The results of the DFT studies on the mechanism of the PIII/PV=O catalyzed reductive amination of nitrosoarenes using ArB(OH)2 yielding diaryl amines are reported. This allowed a comparison of the reaction paths and key intermediates of the Cu(I)- and P(III)-mediated reductive aminations of aryl boronic acids using alkylnitrites, nitroso- or nitroarenes, and revealed important similarities in the catalytic reactivity of transition-metal and main-group elements in C(sp2)–N bond-forming reactions. It is shown that both transformations occur via ambiphilic nitrenoid-type key intermediates, the reactivity of which towards the aryl boronic acid is attributed to the presence of both a Lewis acid center (Cu or P) and a Lewis base center (the N or O atoms of the ‘N=O’ component).
Key words
C–N coupling - nitrenoids - diarylamines - main group catalysis - transition metal catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690893.
- Supporting Information
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