Journal of Organic Chemistry, volume 84, issue 16, pages 9984-9994
Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids
Publication type: Journal Article
Publication date: 2019-07-18
Journal:
Journal of Organic Chemistry
Q2
Q1
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
A novel and efficient AgNO3-facilitated oxidative C-C σ-bond difunctionalization of alkylidenecyclopropanes with α-ketoacids for preparing 2-acyl-substituted 3,4-dihydronaphthalenes is developed. This radical acylation/arylation transformation proceeds via decarboxylation of the α-ketoacid, acylation of the carbon-carbon double bond, cleavage of the carbon-carbon σ-bond, and cyclization with a connected aromatic ring and offers a mild and facile strategy for acylation/arylation of carbon-carbon σ-bonds with an acyl radical and an aromatic ring to build two new carbon-carbon bonds. This method uses an inexpensive oxidant, features a wide substrate scope, and is operationally simple.
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Liu Yu. et al. Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids // Journal of Organic Chemistry. 2019. Vol. 84. No. 16. pp. 9984-9994.
GOST all authors (up to 50)
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Liu Yu., Chen Z., Wang Q., Zhou C., Xiong B., Yang C. A., Tang K. Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids // Journal of Organic Chemistry. 2019. Vol. 84. No. 16. pp. 9984-9994.
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TY - JOUR
DO - 10.1021/acs.joc.9b01125
UR - https://doi.org/10.1021/acs.joc.9b01125
TI - Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids
T2 - Journal of Organic Chemistry
AU - Liu, Yu
AU - Chen, Zan
AU - Wang, Qiao-Lin
AU - Zhou, Cong-Shan
AU - Xiong, Biquan
AU - Yang, Chang An
AU - Tang, Kewen
PY - 2019
DA - 2019/07/18
PB - American Chemical Society (ACS)
SP - 9984-9994
IS - 16
VL - 84
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2019_Liu,
author = {Yu Liu and Zan Chen and Qiao-Lin Wang and Cong-Shan Zhou and Biquan Xiong and Chang An Yang and Kewen Tang},
title = {Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.joc.9b01125},
number = {16},
pages = {9984--9994},
doi = {10.1021/acs.joc.9b01125}
}
Cite this
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Liu, Yu., et al. “Synthesis of 2-Acyl-3,4-dihydronaphthalenes by Silver-Promoted Oxidative C–C σ-Bond Acylation/Arylation of Alkylidenecyclopropanes with α-Ketoacids.” Journal of Organic Chemistry, vol. 84, no. 16, Jul. 2019, pp. 9984-9994. https://doi.org/10.1021/acs.joc.9b01125.