Abstract
The beginning of the 21st century has seen tremendous growth in the field of decarboxylative activation. Benzoic acid derivatives are now recognised as atom‐economic alternatives to traditional cross‐coupling partners, and they also benefit from being inexpensive, readily available and shelf‐stable reagents. In this microreview we discuss recent developments in the coupling of benzoic acid derivatives either with an arene or with a second benzoic acid derivative, a process often termed decarboxylative oxidative cross‐coupling. These procedures offer great promise for the development of highly selective and atom‐economic cross‐couplings.
Highlights
The advent of traditional cross-coupling reactions – coupling between aryl halides and organometallic reagents – revolutionized thoughts relating to the construction of C–C bonds.[1]
Decarboxylative activation is a complementary strategy that can overcome some of the inherent difficulties of C–H activation, because the carboxyl group can provide a handle for selective transformations
The ability of transition metals to promote the decarboxylation of benzoic acid derivatives was first observed in 1930, when Shepard and co-workers noted that furan-2-carboxylic acid derivatives were more prone to protodecarboxylation in the presence of copper than upon heating alone.[4]
Summary
The advent of traditional cross-coupling reactions – coupling between aryl halides and organometallic reagents – revolutionized thoughts relating to the construction of C–C bonds.[1] More recent developments in the areas of C–H activation and decarboxylative activation have looked to improve the atom economy of these procedures by using more simple and readily available reagents.[2,3] The field of C–H activation has provoked considerable interest, because – ideally – it would allow for the construction of complex molecules from the simplest starting ma-. In reality, this methodology faces the significant challenge of selective activation of one C– H bond in the presence of many others. Decarboxylative activation is a complementary strategy that can overcome some of the inherent difficulties of C–H activation, because the carboxyl group can provide a handle for selective transformations. The ready availability of benzoic acid derivatives makes these processes comparable to C–H activation in terms of cost and atom efficiency
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