Journal of Organic Chemistry, volume 84, issue 9, pages 5413-5424
Oxone-Mediated Radical C–C Bond Acetmethylation/Arylation of Methylenecyclopropanes and Vinylcyclopropanes with α-Alkyl Ketones: Facile Access to Oxoalkyl-Substituted 3,4-Dihydronaphthalenes
Yu Liu
1
,
Qiao-Lin Wang
1
,
Zan Chen
1
,
Quan Zhou
1
,
Hua Li
1
,
Wen Yuan Xu
1
,
Biquan Xiong
1
,
Kewen Tang
1
Publication type: Journal Article
Publication date: 2019-03-25
Journal:
Journal of Organic Chemistry
Q2
Q1
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
An efficient oxone-mediated radical carbon-carbon σ-bond acetmethylation/arylation of methylenecyclopropanes with α-C(sp3)-H bonds of ketones is described for the preparation of 2-(2-oxopropyl)-3,4-dihydronaphthalenes. This acetmethylation/arylation undergoes a series of α-C(sp3)-H bond activation, carbon-carbon double bond acetmethylation, carbon-carbon σ-bond cleavage, and cyclization with intramolecular aromatic ring. The experimental result indicates that the carbon-carbon σ-bond acetmethylation/arylation transformation contains a radical process. The difunctionalization method can also be applied to carbon-carbon σ-bond acetmethylation/arylation of vinylcyclopropanes with ketones. This strategy offers an efficient and convenient method for acetmethylation/arylation of a carbon-carbon σ-bond with a α-carbonyl radical and an aromatic carbon in one pot, building two new carbon-carbon bonds.
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Liu Yu. et al. Oxone-Mediated Radical C–C Bond Acetmethylation/Arylation of Methylenecyclopropanes and Vinylcyclopropanes with α-Alkyl Ketones: Facile Access to Oxoalkyl-Substituted 3,4-Dihydronaphthalenes // Journal of Organic Chemistry. 2019. Vol. 84. No. 9. pp. 5413-5424.
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Liu Yu., Wang Q., Chen Z., Zhou Q., Li H., Xu W. Y., Xiong B., Tang K. Oxone-Mediated Radical C–C Bond Acetmethylation/Arylation of Methylenecyclopropanes and Vinylcyclopropanes with α-Alkyl Ketones: Facile Access to Oxoalkyl-Substituted 3,4-Dihydronaphthalenes // Journal of Organic Chemistry. 2019. Vol. 84. No. 9. pp. 5413-5424.
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TY - JOUR
DO - 10.1021/acs.joc.9b00407
UR - https://doi.org/10.1021/acs.joc.9b00407
TI - Oxone-Mediated Radical C–C Bond Acetmethylation/Arylation of Methylenecyclopropanes and Vinylcyclopropanes with α-Alkyl Ketones: Facile Access to Oxoalkyl-Substituted 3,4-Dihydronaphthalenes
T2 - Journal of Organic Chemistry
AU - Liu, Yu
AU - Wang, Qiao-Lin
AU - Chen, Zan
AU - Zhou, Quan
AU - Li, Hua
AU - Xu, Wen Yuan
AU - Xiong, Biquan
AU - Tang, Kewen
PY - 2019
DA - 2019/03/25
PB - American Chemical Society (ACS)
SP - 5413-5424
IS - 9
VL - 84
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2019_Liu,
author = {Yu Liu and Qiao-Lin Wang and Zan Chen and Quan Zhou and Hua Li and Wen Yuan Xu and Biquan Xiong and Kewen Tang},
title = {Oxone-Mediated Radical C–C Bond Acetmethylation/Arylation of Methylenecyclopropanes and Vinylcyclopropanes with α-Alkyl Ketones: Facile Access to Oxoalkyl-Substituted 3,4-Dihydronaphthalenes},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.joc.9b00407},
number = {9},
pages = {5413--5424},
doi = {10.1021/acs.joc.9b00407}
}
Cite this
MLA
Copy
Liu, Yu., et al. “Oxone-Mediated Radical C–C Bond Acetmethylation/Arylation of Methylenecyclopropanes and Vinylcyclopropanes with α-Alkyl Ketones: Facile Access to Oxoalkyl-Substituted 3,4-Dihydronaphthalenes.” Journal of Organic Chemistry, vol. 84, no. 9, Mar. 2019, pp. 5413-5424. https://doi.org/10.1021/acs.joc.9b00407.