ThioleneReaktionen

Thiolene reactions, also known as thiol-ene click chemistry, are a class of highly efficient and versatile reactions that involve the addition of a thiol (R-SH) across a carbon-carbon double bond (alkene). This reaction is characterized by its rapid rate, high yield, tolerance of various functional groups, and mild reaction conditions, making it a valuable tool in organic synthesis and materials science.

The mechanism typically proceeds via a radical or anionic pathway. In the radical pathway, initiation is usually achieved using UV light or a radical initiator. The initiator abstracts a hydrogen atom from the thiol, generating a thiyl radical (RS•). This radical then adds to the alkene, forming a carbon-centered radical. This radical abstracts a hydrogen atom from another thiol molecule, propagating the chain reaction and forming the thioether product. The anionic pathway is typically base-catalyzed, where a strong base deprotonates the thiol to form a thiolate anion (RS-), which then nucleophilically attacks the alkene.

Thiolene reactions have found widespread applications in areas such as polymer synthesis, surface modification, bioconjugation, and the development of functional materials. Their ability to proceed under mild conditions and with high specificity allows for the precise construction of complex molecules and materials. The "click chemistry" designation highlights the reaction's reliability and efficiency, making it a preferred method for connecting molecular building blocks.