Sodium Methyl Carbonate as an Effective C1 Synthon. Synthesis of Carboxylic Acids, Benzophenones, and Unsymmetrical Ketones
Reported is the synthesis of carboxylic acids, symmetrical ketones, and unsymmetrical ketones with selectivity achieved by exploiting the differential reactivity of sodium methyl carbonate with Grignard and organolithium reagents.
Hurst, Timothy E.,Deichert, Julie A.,Kapeniak, Lucas,Lee, Roland,Harris, Jesse,Jessop, Philip G.,Snieckus, Victor
Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions
Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α-keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones bearing various substituents could be easily obtained. The introduction of hydroxyl substituent on ortho-site of α-keto acids make this strategy further applicable to the construction of flavone derivatives via heteroannulation in moderate to good yields with a similar silver-catalyzed system. The reactions proceed under relatively mild reaction conditions and tolerate a wide variety of functional groups. Control experiments indicated that both the reactions undergo radical processes. (Figure presented.).
Palladium-Catalyzed Synthesis of Conjugated Allenynes via Decarboxylative Coupling
A new strategy to access conjugated allenynes via a decarboxylative coupling of propargyl esters of propiolates has been developed. In this process, allenyl-palladium intermediates are coupled with acetylides that are generated in situ to form the conjuga
Smith, Mary K.,Tunge, Jon A.
p. 5497 - 5500
(2017/10/25)
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