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Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters

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Abstract

An efficient transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B2(OH)4 reagent not only served as the boron source but also acted as an electron donor source through formation of a complex with a DMAc-like Lewis base. This complex could be used as an efficient single electron reductant in other ring-opening transformations of cycloketone oxime esters. Free-radical trapping, radical-clock, and DFT calculations all suggest a radical pathway for this transformation.

Graphical abstract: Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters

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Publication details

The article was received on 26 Jul 2018, accepted on 28 Sep 2018 and first published on 02 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC03315C
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters

    J. Zhang, X. Duan, Y. Wu, J. Yang and L. Guo, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C8SC03315C

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