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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.
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)
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 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. [1] [2] This is
The reaction mechanism involves a two-stage radical process: electrochemical decarboxylation gives a radical intermediate, which combine to form a covalent bond. [2] As an example, electrolysis of acetic acid yields ethane and carbon dioxide: CH 3 COOH → CH 3 COO − → CH 3 COO· → CH 3 · + CO 2 2CH 3 · → CH 3 CH 3
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.
Ketonic decarboxylation (also known as decarboxylative ketonization) is a type of organic reaction involving decarboxylation, converting two equivalents of a carboxylic acid (R−C(=O)OH) to a symmetric ketone (R 2 C=O). The reaction typically requires heat and a metal catalyst, and generally proceeds in low yields.
Usually, they are named after the substrate whose decarboxylation they catalyze, for example pyruvate decarboxylase catalyzes the decarboxylation of pyruvate. Examples [ edit ]
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