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

被引:247
作者
Chan, Justin W. [1 ]
Hoyle, Charles E. [1 ]
Lowe, Andrew B. [1 ]
机构
[1] Univ So Mississippi, Sch Polymers & High Performance Mat, Hattiesburg, MS 39406 USA
关键词
CLICK CHEMISTRY; POLYMERS; FUNCTIONALIZATION; HYDROTHIOLATION; ALKYNES;
D O I
10.1021/ja8099135
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:5751 / +
页数:4
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