Organic Letters
Organic Letters
5 years ago

Iron-Catalyzed Oxidative C–H Functionalization of Internal Olefins for the Synthesis of Tetrasubstituted Furans

Iron-Catalyzed Oxidative C–H Functionalization of Internal Olefins for the Synthesis of Tetrasubstituted Furans
Kaikai Wu, Ping Wu, Quannan Wang, Jiang Lou, Zhengkun Yu
Tetrasubstituted furans were efficiently synthesized from Fe(OAc)2-catalyzed C–H/C–H cross-dehydrogenative-coupling (CDC) reactions of activated carbonyl methylenes with S,S-functionalized internal olefins, that is, α-oxo ketene dithioacetals and analogues, under oxidative conditions. β-Ketoesters, 1,3-dicarbonyls, β-keto nitrile, and amide derivatives were used as the coupling partners. The resultant alkylthio- and carbonyl-functionalized furans could be further transformed to diverse arylated furan derivatives and furan-fused N-heterocycles, respectively. The control experiments have revealed a radical reaction pathway.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01431

DOI: 10.1021/acs.orglett.7b01431

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