Copper(I)/Ligand-Catalyzed 5-endo Radical Cyclization-Aromatization of 2,2,2-Trichloroethyl Vinyl Ethers: Synthesis of 2,3-Difunctionalized 4-Chlorofurans

The Journal of Organic Chemistry
Ram Nath RamVineet Kumar Soni

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.

References

Dec 2, 1999·Journal of Natural Products·Y L LinM S Shiao
Oct 14, 2000·The Journal of Organic Chemistry·V K Aggarwal, A Mereu
Jul 12, 2002·Chemical Society Reviews·Andrew J Clark
Sep 5, 2002·Journal of the American Chemical Society·Chryssostomos ChatgilialogluThanasis Gimisis
Sep 1, 1962·Journal of Medicinal and Pharmaceutical Chemistry·J G MICHELSP H WEI
Apr 6, 2004·Angewandte Chemie·Edward A AndersonErik J Sorensen
Dec 25, 2004·Angewandte Chemie·Richard C D Brown
Apr 5, 2008·Natural Product Reports·Paul A Roethle, Dirk Trauner
May 29, 2008·The Journal of Organic Chemistry·Gang Cheng, Youhong Hu
Jul 4, 2008·Bioorganic & Medicinal Chemistry Letters·Mark E SchnuteJanet L Wieber
Aug 9, 2008·Angewandte Chemie·Timothy J DonohoeNeil M Kershaw
Apr 8, 2009·Journal of Medicinal Chemistry·Qun DangMark D Erion
May 28, 2009·Journal of Medicinal Chemistry·Karen Miller-MoslinJoseph F Kelleher
Sep 30, 2010·The Journal of Organic Chemistry·Ram N RamNem Singh
May 31, 2014·Chemical Communications : Chem Comm·Wei DuZheng-Hui Guan
Mar 19, 2015·Angewandte Chemie·J Stephen ClarkLouis J Farrugia
Aug 19, 2015·Organic Letters·Srimanta Manna, Andrey P Antonchick

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Citations

Sep 2, 2016·Scientific Reports·Shaoxiang YangYanyu Lv
Feb 4, 2021·Angewandte Chemie·Violet Yijang Chen, Ohyun Kwon

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