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

Jin Jiang Zhang; Xin Hua Duan; Yong Wu; Jun Cheng Yang; Li Na Guo

doi:10.1039/C8SC03315C

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

Jin Jiang Zhang
, Xin Hua Duan
, Yong Wu
, Jun Cheng Yang
, Li Na Guo

School of Chemistry

Xi'an Jiaotong University

Research output: Contribution to journal › Article › peer-review

144 Scopus citations

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.

Original language	English
Pages (from-to)	161-166
Number of pages	6
Journal	Chemical Science
Volume	10
Issue number	1
DOIs	https://doi.org/10.1039/C8SC03315C
State	Published - 2019

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10.1039/C8SC03315C

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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.",

author = "Zhang, \{Jin Jiang\} and Duan, \{Xin Hua\} and Yong Wu and Yang, \{Jun Cheng\} and Guo, \{Li Na\}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

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doi = "10.1039/C8SC03315C",

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T1 - Transition-metal free C-C bond cleavage/borylation of cycloketone oxime esters

AU - Zhang, Jin Jiang

AU - Duan, Xin Hua

AU - Wu, Yong

AU - Yang, Jun Cheng

AU - Guo, Li Na

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85059074179

U2 - 10.1039/C8SC03315C

DO - 10.1039/C8SC03315C

M3 - 文章

AN - SCOPUS:85059074179

SN - 2041-6520

VL - 10

SP - 161

EP - 166

JO - Chemical Science

JF - Chemical Science

IS - 1

ER -

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

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