1173839-84-3Relevant academic research and scientific papers
Facile synthesis of 4-substituted 3,4-dihydrocoumarins via an organocatalytic double decarboxylation process
Peng, Shiyong,Wang, Lei,Guo, Haibing,Sun, Shaofa,Wang, Jian
supporting information; experimental part, p. 2537 - 2541 (2012/04/23)
3,4-Dihydrocoumarins, considered to be valuable building blocks, have attracted considerable attention due to their various biological activities. Herein, we have documented an efficient and convenient double decarboxylation process for the synthesis of 4-substituted 3,4-dihydrocoumarin in moderate to excellent yields under mild reaction conditions (up to 98%). The Royal Society of Chemistry 2012.
Decarboxylative ketone aldol reactions: Development and mechanistic evaluation under metal-free conditions
Blaquiere, Nicole,Shore, Daniel G.,Rousseaux, Sophie,Fagnou, Keith
supporting information; experimental part, p. 6190 - 6198 (2009/12/24)
(Chemical Equation Presented) Malonic acid half thioesters (MAHTs) and malonic acid half oxyesters (MAHOs) are shown to undergo decarboxylative nucleophilic addition reactions with ketone and aldehyde electrophiles in the presence of stoichiometric or catalytic quantities of triethylamine at room temperature. The ability to perform these reactions under metal-free conditions has enabled a detailed mechanistic analysis of the reaction pathway leading to the 1H NMR spectroscopic characterization of a postnucleophilic addition/predecarboxylation intermediate and experimental evidence for a reversible formation of this intermediate followed by an irreversible decarboxylation. Rate constants for each of the bond forming/bond breaking steps in the reaction pathway were also determined, casting light on the differing reactivity betweenMAHOandMAHT nucleophiles in these processes. Finally, the mechanistic insights gained through these studies have been employed in the development of a new decarboxylative coumarin synthesis.
