Decarboxylative homocoupling of (hetero)aromatic carboxylic acids

Abstract

A variety of hetero(aromatic) carboxylic acids are shown to undergo decarboxylative homocoupling, mediated by a Pd/Ag system. This novel methodology for the synthesis of symmetrical biaryls avoids the use of haloarenes and organometallic compounds as starting materials.

Transition metal-catalyzed decarboxylative cross-coupling reactions

“…On the other hand, the decarboxylative homo-coupling of a single carboxylic acid is practically useful for the preparation of some symmetric molecules. For instance, Larrosa et al described the Pd-catalyzed decarboxylative homo-coupling of aromatic carboxylic acids (Scheme 54) [68]. Symmetric biphenyls are produced in the reaction without the use of aryl halides or organometallic reagents.…”

Decarboxylative Coupling Techniques

“…Further improvement of the reaction conditions allowed extending the substrate scope to less expensive aryl tosylates, using Pd(acac) 2 , the sterically electron-rich XPhos ligand, Cu 2 O, and Scheme 3.14 Decarboxylative homocoupling of (hetero)aromatic carboxylic acids, as described by Larrosa and coworkers [28].…”

Palladium‐Catalyzed Decarboxylative Suzuki and Heck Couplings of Azaindole‐2‐carboxylic Acids: Synthesis of 2‐Aryl/Alkenyl‐1‐phenylsulfonyl‐1 H‐pyrrolo‐[2,3 b]pyridines

“…(2)). [8] Although a number of decarboxylative couplings have been demonstrated, new and efficient strategies are desirable. One such reaction in which a carboxylic acid undergoes coupling with an inorganic acid, such as an aryl boronic acid, to deliver a biaryl system was conceived and this new process was conceptually termed a decarboxylative Suzuki-type coupling (Scheme 1, Eq.…”