Recent Advances in Decarboxylative Reactions of Alkynoic Acids

Abstract

Alkynoic acids have been widely employed as alkyne and alkene sources in decarboxylative reactions. Alkynoic acid coupling leads to the formation of direct coupling products and cyclized products through sequential reactions. Moreover, homocoupling and multicomponent reactions have been developed. The decarboxylative addition of alkynoic acids generates the corresponding alkene products. A number of synthetic methods are utilized for the preparation of arylpropynoic acids including the Sonogashira coupling and the carboxylation of terminal alkynes. Recently, the use of decarboxylative halogenations has also been reported. This review covers decarboxylative reactions of alkynoic acids reported between 2013 and 2019; further, it is divided into several sections according to the type of reaction.1 Introduction2 Direct Coupling3 Sequential Reactions4 Homocoupling5 Multicomponent Reactions6 Addition7 Halogenations8 Synthesis of Alkynoic Acids9 Conclusion

N-Alkylation/aldol reaction of α-aldimino thioesters: a facile three-component coupling reaction

“… 14 Since the present procedure offers a rapid assembly of three components efficiently, this methodology is useful in addition to the existing precedents for the synthesis of 1,2-hydroxy amines 1,2 and 1,2-diamines. 15 …”

Transition metal-catalyzed alkynylation reactions via alkynyl carbon–carbon bond cleavage

“…Lee and co-workers have previously reviewed the transition metal-catalyzed decarboxylative coupling reactions of propiolic acids. 7 a ,11 Therefore, herein we will only briefly summarize the research progress of alkynylation via transition metal-catalyzed decarboxylative coupling reaction of alkynoic acids, mostly those published since 2020.…”

Iron-photocatalyzed double decarboxylative coupling reactions of alkynoic acids and alkyl carboxylic acids: access to alkylated alkynes

“…2 Since then, several research groups, including ours, have developed diverse coupling partners, including both carbon-based molecules and heteroatom-based molecules. 3 In particular, numerous aryl reagents have been used in the decarboxylative coupling reactions of alkynyl carboxylic acids, enabling the formation of sp 2 –sp carbon bonds. 4 However, alkylating agents have rarely been used as coupling partners in the decarboxylative reactions of alkynyl carboxylic acids.…”