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Issue 8, 2010
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Reduction of base-stabilized difluoroboranes to induce rearrangement reactions

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Abstract

Lewis base-stabilized difluoroboranes 2, 4-pyr and 4-iPr, having an oxazoline- or amine-tethered amide ligand, were synthesized and fully characterized. The treatment of 2 with KC8 led to its complete consumption, and the rearranged product 5-H, probably originating from C–O bond cleavage and B–O bond formation, could be isolated as a major Dip-containing product in 18% yield. From deuterium labelling experiments and diffusion control reactions, the formation of 5-H could be explained by a radical mechanism. The reduction of 4-pyr and 4-iPr using one-electron reducing agents also gave the rearranged products 13-pyr and 13-iPr in 21 and 19% yields, respectively, via C–N bond cleavage and B–N bond formation. The mechanism for the formation of 13-pyr and 13-iPr is suggested to contain a benzylic radical intermediate.

Graphical abstract: Reduction of base-stabilized difluoroboranes to induce rearrangement reactions

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Publication details

The article was received on 13 May 2010, accepted on 06 Jul 2010 and first published on 09 Jul 2010


Article type: Paper
DOI: 10.1039/C0NJ00363H
Citation: New J. Chem., 2010,34, 1774-1782
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    Reduction of base-stabilized difluoroboranes to induce rearrangement reactions

    M. Yamashita, Y. Aramaki and K. Nozaki, New J. Chem., 2010, 34, 1774
    DOI: 10.1039/C0NJ00363H

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