Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 49, Pages 19981-19984Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja309446n
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Funding
- NSF [CHE-1152767]
- NIH [R01-GM098777]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1624211, 1152767] Funding Source: National Science Foundation
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Co(III)-carbene radicals generated from activation of alpha-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-Di(t)Bu-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 alpha-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 alpha-oligofurans.
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