Issue 1, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
26 Jūl. 2018
Accepted
28 Sept. 2018
First published
02 Okt. 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 161-166

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., 2019, 10, 161 DOI: 10.1039/C8SC03315C

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