Synthesis of 4H-cyclopenta[c]furan-5(6H)-one derivatives

In Ph3PAuCl/AgOTf/TsOH system, 2-diazo-5-alkynyl-1,7-diketo carbonyl compounds were transformed into diazo furans. Rh2(OAc)4-mediated conversion of the diazo furan derivatives into 4H-cyclopenta[c]furan-5(6H)-one derivatives was accomplished via C(sp2)−H insertion reaction at 4-position on the furan...

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Bibliographic Details
Published in:Tetrahedron 2020-08, Vol.76 (35), p.131421, Article 131421
Main Authors: Tu, Xianxia, Peng, Haiyun, Deng, Guisheng
Format: Article
Language:English
Subjects:
4H-cyclopenta[c]furan-5(6H)-one derivatives
C(sp2)−H insertion
Diazo compounds
Synthesis
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Summary:In Ph3PAuCl/AgOTf/TsOH system, 2-diazo-5-alkynyl-1,7-diketo carbonyl compounds were transformed into diazo furans. Rh2(OAc)4-mediated conversion of the diazo furan derivatives into 4H-cyclopenta[c]furan-5(6H)-one derivatives was accomplished via C(sp2)−H insertion reaction at 4-position on the furan ring. [Display omitted] •The method involves the construction of furan cycle and selective C(sp2)-H insertion of metal carbene on furan ring.•It is the first example of C(sp2)-H insertion on furan ring.•This protocol has several advantages, such as mild reaction conditions and simple experimental process.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131421