Title

Regioselective Synthesis of Multisubstituted Furans via Metalloradical Cyclization of Alkynes with α-Diazocarbonyls: Construction of Functionalized α-Oligofurans

Document Type

Article

Publication Date

2012

Digital Object Identifier (DOI)

https://doi.org/10.1021/ja309446n

Abstract

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.

Was this content written or created while at USF?

Yes

Citation / Publisher Attribution

Journal of the American Chemical Society, v. 134, issue 49, p. 19981-19984

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