Journal
CHEMICAL SCIENCE
Volume 10, Issue 1, Pages 161-166Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc03315c
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Funding
- Natural Science Basic Research Plan in Shaanxi Province of China [2016JZ002]
- Fundamental Research Funds of the Central Universities [zrzd2017001, xjj2016056]
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An efficient transition-metal free C-C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B-2(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.
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