Advances in organocatalysis of the Michael reaction by tertiary Phosphines

Tertiary phosphines have been recognized as powerful organocatalysts for the Michael reaction, which is one of the most important atom-economical methods for carbon-carbon and carbon-heteroatom bond construction. In the presence of tertiary phosphines, a vast array of Michael acceptors and Michael donors can be coupled with each other under neutral and metal-free conditions to produce useful densely functionalized molecules. This review highlights the role of phosphine-catalyzed Michael reaction in cutting-edge areas, such as asymmetric synthesis, natural products synthesis, drug design, and polymer material science. As the central part of catalysis science, the kinetic and mechanistic issues are also discussed when possible. The review is organized by the type of the Michael acceptor and the Michael donor used in the reaction.

Automated summary

Tertiary phosphines are powerful organocatalysts for the Michael reaction, which is a highly important atom-economical method for carbon-carbon and carbon-heteroatom bond construction. Under neutral and metal-free conditions, a wide range of Michael acceptors and donors can be coupled together using tertiary phosphines, leading to the synthesis of densely functionalized molecules. This review focuses on the role of phosphine-catalyzed Michael reactions in cutting-edge areas such as asymmetric synthesis, natural products synthesis, drug design, and polymer material science. The review is organized according to the type of Michael acceptor and donor used in the reaction, and also discusses the kinetic and mechanistic issues when possible.