A dearomatization strategy has been developed for the efficient construction of vertically expanded five-ring fused benzofurans from ortho-alkynylphenols and ortho-alkynylarylaldimines. The stepwise procedure comprises a dearomatization-induced silver-catalyzed [3 + 2] cycloaddition followed by an aromatization-triggered ytterbium-catalyzed rearrangement.
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Stereoselective Synthesis of Acyclic Tetrasubstituted Alkenes from Anilines by Dearomatization and Trimethylenemethane Cycloaddition.
Org Lett
January 2022
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, China.
A method for stereoselective construction of acyclic all-carbon tetrasubstituted alkenes through insertion of nitrile-substituted trimethylenemethane into the aryl C-N bond in anilines via an aromaticity destruction-reconstruction process is reported. The process involves dearomatization, azo-[3 + 2] TMM cycloaddition and aromatization-triggered rearrangement.
View Article and Find Full Text PDFDearomatization-Induced Cycloaddition and Aromatization-Triggered Rearrangement: Synthesis of Vertically Expanded Five-Ring Fused Benzofurans.
Org Lett
September 2016
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China.
A dearomatization strategy has been developed for the efficient construction of vertically expanded five-ring fused benzofurans from ortho-alkynylphenols and ortho-alkynylarylaldimines. The stepwise procedure comprises a dearomatization-induced silver-catalyzed [3 + 2] cycloaddition followed by an aromatization-triggered ytterbium-catalyzed rearrangement.
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