Sequential Phosphine-Catalyzed, Nucleophilic Thiol−Ene/Radical-Mediated Thiol−Yne Reactions and the Facile Orthogonal Synthesis of Polyfunctional Materials

作者：Justin W. Chan, Charles E. Hoyle, Andrew B. Lowe · 发表于：Journal of the American Chemical Society · 年份：2009 · DOI：10.1021/ja8099135 · 被引用次数：276 · 研究领域：Sulfur-Based Synthesis Techniques、Click Chemistry and Applications、Chemical Synthesis and Reactions

The first example of highly efficient sequential thiol-ene/thiol-yne reactions conducted in an orthogonal manner is presented and its broad application in the synthesis of polyfunctional materials demonstrated. The anionic chain mechanism of the phosphine-mediated thiol-ene reaction is highlighted, as is the radical-mediated thiol-yne reaction. Kinetic data for a model reaction are presented, followed by a discussion of the synthesis of a range of materials with diverse functionality, including an example of potential biomedical significance.