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Attempted one-pot amination of the simplest tertiary boronic ester 2aa according to Ref. [6e] gave the desired amine but only in moderate yield (50a%), whereas subjecting the trifluoroborate salt 3aa to Matteson's original protocol afforded amine 5aaa in considerably higher yield (74a%). Furthermore, any trifluoroborate salt is readily available from the respective pinacolboronic ester in essentially quantitative yield.
-
Attempted one-pot amination of the simplest tertiary boronic ester 2aa according to Ref. [6e] gave the desired amine but only in moderate yield (50a%), whereas subjecting the trifluoroborate salt 3aa to Matteson's original protocol afforded amine 5aaa in considerably higher yield (74a%). Furthermore, any trifluoroborate salt is readily available from the respective pinacolboronic ester in essentially quantitative yield:, V. Bagutski, A. Ros, V. K. Aggarwal, Tetrahedron 2009, 65, 9956-9960.
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Toluene was the original solvent but we have found 1,2-dichloroethane to be the solvent of choice. For the use of DCE in aminations of dichloroboranes see also.
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For the preparation of the title trifluoroborate and its subsequent amination see Supporting Information.
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