Three Component syn-1,2-Arylmethylation of Internal Alkynes** |
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Authors: | Dr. Shubham Dutta Prof. Dr. Akhila K. Sahoo |
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Affiliation: | School of Chemistry, University of Hyderabad, Hyderabad, 500046 India |
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Abstract: | A Pd-catalyzed three-component syn-1,2-arylmethylation of internal alkynes (ynamides/yne-acetates/alkynes) is described. The readily available and bench stable coupling partners iodo-arenes, and methyl boronic acid are successfully used in this coupling strategy to access the methyl-containing tetra-substituted olefins; the scope is broad showing excellent functional-group tolerance. Notably, the transformation is regio- as well as stereoselective. The biologically relevant motifs (BRM) bearing iodo-arenes and ynamides are also used for the late-stage syn-1,2-arylmethylation of alkynes. Aryl-alkylation, aryl-trideuteriomethylation, alkynyl-methylation, and alkenyl-methylation of ynamides are also presented. The Me-substituted alkenes are further transformed into synthetically important β-amino-indenones and α-fluoro-α′-methyl ketones. |
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Keywords: | Methylation Multicomponent Reaction Palladium Catalysis Regioselectivity Unsymmetrical Alkynes |
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