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Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO 2). Usually, decarboxylation refers to a reaction of carboxylic acids , removing a carbon atom from a carbon chain.
Studies of decarboxylation over nickel and palladium-based catalysts were first reported by Wilhelm Maier et al., in 1982, [6] when they achieved the deoxygenation of several carboxylic acids via decarboxylation under a hydrogen atmosphere. This included the conversion of aliphatic acids (such as heptanoic and octanoic acids) to alkanes (namely ...
The first reported decarboxylative cross coupling reaction was an Ullmann reaction, in 1966 by Nilsson et al. Thermal decarboxylation of copper benzoates, in the presence of an aryl halide, was found to produce (both symmetric and unsymmetric) biaryls through aryl-Cu intermediates. [2] First reported decarboxylative Ullmann coupling (Nilsson, 2005)
In the absence of metal catalysts, decarbonylation (vs decarboxylation) is rarely observed in organic chemistry. One exception is the decarbonylation of formic acid: H CO OH → CO + H 2 O. The reaction is induced by sulfuric acid, which functions as both a catalyst and a dehydrating agent.
In contrast to the relatively facile decarboxylation of β-keto acids, the decarboxylation of α-keto acids presents a mechanistic challenge. Thiamine pyrophosphate (TPP) provides the biochemical and enzymological answer. TPP is the key catalytic cofactor used by enzymes catalyzing non-oxidative and oxidative decarboxylation of α-keto acids.
Usually, they are named after the substrate whose decarboxylation they catalyze, for example pyruvate decarboxylase catalyzes the decarboxylation of pyruvate. Examples [ edit ]
The Barton decarboxylation is a radical reaction in which a carboxylic acid is converted to a thiohydroxamate ester (commonly referred to as a Barton ester). The product is then heated in the presence of a radical initiator and a suitable hydrogen donor to afford the decarboxylated product.
The Tsuji–Wilkinson decarbonylation reaction is a method for the decarbonylation of aldehydes and some acyl chlorides.The reaction name recognizes JirÅ Tsuji, whose team first reported the use of Wilkinson's catalyst (RhCl(PPh 3) 3) for these reactions: