Transition-Metal-Free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds

A novel ring expansion reaction of indene-1,3-dione with alkynyl ketones under transition-metal-free conditions has been developed. This process offers an efficient and direct way to synthesize benzoannulated seven-membered rings or fused-ring compounds through C–C σ-bond activation. Notable feature...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 7; pp. 1744 - 1747
Main Authors Yao, Qiyi, Kong, Lingkai, Wang, Mengdan, Yuan, Yang, Sun, Ruizhuo, Li, Yanzhong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.04.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ARYNE INSERTION
PROMOTED TANDEM REACTION
ACTIVATION
BETA-KETOESTERS
CATALYZED SYNTHESIS
CARBON SIGMA-BONDS
CHROMONE DERIVATIVES
ALKYNES
SINGLE-BOND
C-C CLEAVAGE
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Summary:A novel ring expansion reaction of indene-1,3-dione with alkynyl ketones under transition-metal-free conditions has been developed. This process offers an efficient and direct way to synthesize benzoannulated seven-membered rings or fused-ring compounds through C–C σ-bond activation. Notable features of the procedure include easily accessible starting materials, good functional group tolerance, and high atom economy.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00206