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Chemoselective Primary Amination of Aryl Boronic Acids by PIII/PV═O-Catalysis: Synthetic Capture of the Transient Nef Intermediate HNO.

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A catalytic approach to intercept the transient HNO for a chemoselective primary amination of arylboronic acids is reported. A phosphetane-based catalyst operating within PIII/PV═O redox cycling is shown to capture… Click to show full abstract

A catalytic approach to intercept the transient HNO for a chemoselective primary amination of arylboronic acids is reported. A phosphetane-based catalyst operating within PIII/PV═O redox cycling is shown to capture HNO, generated in situ by Nef decomposition of 2-nitropropane, to selectively install the primary amino group at aryl Csp2 centers. The method furnishes versatile primary arylamines from arylboronic acid substrates with the preservation of otherwise reactive functional groups.

Keywords: chemoselective primary; transient; primary amination; hno; capture

Journal Title: Journal of the American Chemical Society
Year Published: 2022

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