Barton decarboxylation

What is Barton decarboxylation?

The Barton decarboxylation is a two-step process that involves the radical decarboxylation of organic acids to produce alkanes. In 1983, Barton first reported this reaction, which generates thiohydroxamic acid esters of the organic acid, followed by the addition of a radical initiator and reagents that provide a good H-atom donor, such as tri-n-butyltin hydride, t-butylmercaptan, phenylselenol, and tri(trimethylsilyl)silane. Barton decarboxylation is a chemical reaction that involves the removal of a carboxyl group (-COOH) from an organic compound.

Barton decarboxylation - general reaction scheme - Barton's radical decarboxylation
Barton decarboxylation

The Barton decarboxylation is also referred to as Barton’s radical decarboxylation. Notably, THF is not suitable as an H-atom donor, and the reaction can be initiated through photolysis or sonication, as well as through the use of a radical initiator (see list of acronyms).