Metal-Free Oxidative Radical Alkynylation/Ring Expansion Rearrangement of Alkenyl Cyclobutanols with Ethynylbenziodoxolones

The first metal-free alkynylation/ring expansion cascade process of alkenyl cyclobutanols with ethynylbenziodoxolones has been developed. A variety of synthetically valuable β-alkynylated cyclopentanones were prepared in moderate to good yields. Alkynyl cyclobutanols could also undergo this transfor...

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Published inOrganic letters Vol. 18; no. 16; pp. 4024 - 4027
Main Authors Zhang, Ruo-Yi, Xi, Long-Yi, Shi, Lei, Zhang, Xiao-Zhuan, Chen, Shan-Yong, Yu, Xiao-Qi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.08.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
ETHYNYLATION
2-ALKYLIDENECYCLOPENTANONES
STRATEGY
VISIBLE-LIGHT PHOTOREDOX
CONSTRUCTION
ARENES
ALDEHYDES
BOND-CLEAVAGE
C-H ALKYNYLATION
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Summary:The first metal-free alkynylation/ring expansion cascade process of alkenyl cyclobutanols with ethynylbenziodoxolones has been developed. A variety of synthetically valuable β-alkynylated cyclopentanones were prepared in moderate to good yields. Alkynyl cyclobutanols could also undergo this transformation, providing a new approach to substituted ene-yne-carbonyl compounds.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01856