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

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 co...

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Autores principales: Zhang, Jin-Jiang, Duan, Xin-Hua, Wu, Yong, Yang, Jun-Cheng, Guo, Li-Na
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6328001/
https://www.ncbi.nlm.nih.gov/pubmed/30713627
http://dx.doi.org/10.1039/c8sc03315c
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author Zhang, Jin-Jiang
Duan, Xin-Hua
Wu, Yong
Yang, Jun-Cheng
Guo, Li-Na
author_facet Zhang, Jin-Jiang
Duan, Xin-Hua
Wu, Yong
Yang, Jun-Cheng
Guo, Li-Na
author_sort Zhang, Jin-Jiang
collection PubMed
description 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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spelling pubmed-63280012019-02-01 Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters Zhang, Jin-Jiang Duan, Xin-Hua Wu, Yong Yang, Jun-Cheng Guo, Li-Na Chem Sci Chemistry 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. Royal Society of Chemistry 2018-10-02 /pmc/articles/PMC6328001/ /pubmed/30713627 http://dx.doi.org/10.1039/c8sc03315c Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Zhang, Jin-Jiang
Duan, Xin-Hua
Wu, Yong
Yang, Jun-Cheng
Guo, Li-Na
Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters
title Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters
title_full Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters
title_fullStr Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters
title_full_unstemmed Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters
title_short Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters
title_sort transition-metal free c–c bond cleavage/borylation of cycloketone oxime esters
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6328001/
https://www.ncbi.nlm.nih.gov/pubmed/30713627
http://dx.doi.org/10.1039/c8sc03315c
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