Journal
ORGANIC LETTERS
Volume 20, Issue 16, Pages 4801-4805Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01956
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Funding
- NSFC [21302044, U1304524, U1604285]
- China Postdoctoral Science Foundation Funded Project [2015T80769]
- Program for Science AMP
- Technology Innovation Talents in Universities of Henan Province [18HASTIT006]
- 111 Project [D17007]
- Outstanding Youth Science Project Funding of Henan Normal University [14YQ004]
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The first umpolung strategy for the cycloacylation of fullerene using a N-heterocyclic carbene organocatalyst is reported. The coupling of [60]fullerene with different structural alpha,beta-unsaturated aldehydes efficiently furnishes interesting [60]fullerene-fused cyclopentan-1-ones or cyclohex-2-en-1-ones in good to excellent yields. This new reaction displays a wide substrate scope and excellent functional group tolerance, and diverse substituents such as aryl, heteroaryl, alkenyl, alkyl, and ester can be installed by using the corresponding enals.
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