Regioselective Synthesis of Multisubstituted Furans via Metalloradical Cyclization of Alkynes with α-Diazocarbonyls: Construction of Functionalized α-Oligofurans
Digital Object Identifier (DOI)
Co(III)–carbene radicals generated from activation of α-diazocarbonyls by Co(II)–porphyrin complexes have been shown to undergo a new type of tandem radical addition reaction with alkynes that affords five-membered furan structures. The Co(II) complex of 3,5-DitBu-IbuPhyrin, [Co(P1)], is effective in catalyzing the metalloradical cyclization reaction under neutral and mild conditions. The [Co(P1)]-catalyzed process tolerates a wide range of α-diazocarbonyls and terminal alkynes with varied steric and electronic properties, producing polyfunctionalized furans with complete regioselectivity. The catalytic synthesis features a high degree of functional group tolerance and can be applied iteratively to construct functionalized α-oligofurans.
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Citation / Publisher Attribution
Journal of the American Chemical Society, v. 134, issue 49, p. 19981-19984
Scholar Commons Citation
Cui, Xin; Xu, Xue; Wojtas, Lukasz; Kim, Martin M.; and Zhang, X. Peter, "Regioselective Synthesis of Multisubstituted Furans via Metalloradical Cyclization of Alkynes with α-Diazocarbonyls: Construction of Functionalized α-Oligofurans" (2012). Chemistry Faculty Publications. 172.