Copper(I)/Ligand-Catalyzed 5-endo Radical Cyclization–Aromatization of 2,2,2-Trichloroethyl Vinyl Ethers: Synthesis of 2,3-Difunctionalized 4-Chlorofurans
Publication type: Journal Article
Publication date: 2016-01-29
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
26796068
Organic Chemistry
Abstract
Copper(I)/ligand-catalyzed one pot synthesis of highly substituted 2,3-difunctionalized-4-chlorofurans has been reported. The reaction proceeds via a Cu(I)-catalyzed regioselective 5-endo-trig radical cyclization of 2,2,2-trichloroethyl vinyl ethers followed by the base-promoted dehydrochlorination. The success of the kinetically disfavored 5-endo cyclization was attributed to the formation of captodatively stabilized radical intermediate in the cyclization step and relatively high reaction temperature. Synthetic application of this protocol was also demonstrated in the preparation of alkyl and aryl substituted 4-chlorofuranonapthoquinones.
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Ram R. N., Gupta D. K., Soni V. K. Copper(I)/Ligand-Catalyzed 5-endo Radical Cyclization–Aromatization of 2,2,2-Trichloroethyl Vinyl Ethers: Synthesis of 2,3-Difunctionalized 4-Chlorofurans // Journal of Organic Chemistry. 2016. Vol. 81. No. 4. pp. 1665-1674.
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Ram R. N., Gupta D. K., Soni V. K. Copper(I)/Ligand-Catalyzed 5-endo Radical Cyclization–Aromatization of 2,2,2-Trichloroethyl Vinyl Ethers: Synthesis of 2,3-Difunctionalized 4-Chlorofurans // Journal of Organic Chemistry. 2016. Vol. 81. No. 4. pp. 1665-1674.
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TY - JOUR
DO - 10.1021/acs.joc.5b02830
UR - https://doi.org/10.1021/acs.joc.5b02830
TI - Copper(I)/Ligand-Catalyzed 5-endo Radical Cyclization–Aromatization of 2,2,2-Trichloroethyl Vinyl Ethers: Synthesis of 2,3-Difunctionalized 4-Chlorofurans
T2 - Journal of Organic Chemistry
AU - Ram, Ram N
AU - Gupta, Dharmendra Kumar
AU - Soni, Vineet Kumar
PY - 2016
DA - 2016/01/29
PB - American Chemical Society (ACS)
SP - 1665-1674
IS - 4
VL - 81
PMID - 26796068
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2016_Ram,
author = {Ram N Ram and Dharmendra Kumar Gupta and Vineet Kumar Soni},
title = {Copper(I)/Ligand-Catalyzed 5-endo Radical Cyclization–Aromatization of 2,2,2-Trichloroethyl Vinyl Ethers: Synthesis of 2,3-Difunctionalized 4-Chlorofurans},
journal = {Journal of Organic Chemistry},
year = {2016},
volume = {81},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.joc.5b02830},
number = {4},
pages = {1665--1674},
doi = {10.1021/acs.joc.5b02830}
}
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Ram, Ram N., et al. “Copper(I)/Ligand-Catalyzed 5-endo Radical Cyclization–Aromatization of 2,2,2-Trichloroethyl Vinyl Ethers: Synthesis of 2,3-Difunctionalized 4-Chlorofurans.” Journal of Organic Chemistry, vol. 81, no. 4, Jan. 2016, pp. 1665-1674. https://doi.org/10.1021/acs.joc.5b02830.