Palladium-catalyzed carbon-sulfur or carbon-phosphorus bond metathesis by reversible arylation
Palladium-catalyzed carbon-sulfur or carbon-phosphorus bond metathesis by reversible arylation
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DOI：
10.1126/science.aam9041
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发表时间：
2017-06-09
期刊：
影响因子：
56.9
通讯作者：
Morandi, Bill
中科院分区：
文献类型：
--
作者：
Lian, Zhong;Bhawal, Benjamin N.;Morandi, Bill
带有芳基硫键和芳基磷键的化合物在药物开发、有机材料、聚合物科学和均相催化中有许多应用。我们描述了钯催化的复分解反应的两个化合物类，其中每一个收益通过可逆的芳基化歧管。这种方法的合成功率和直接效用在几个应用程序中得到了证明，这些应用程序通过传统的交叉耦合方法来实现是具有挑战性的。C（sp（2））-S键复分解方案用于商业热塑性聚合物的解聚和药物的后期衍生化。C（sp（2））-P变体通过闭环转化方便地制备了多种磷杂环，包括潜在的手性配体和荧光有机材料。
Compounds bearing aryl-sulfur and aryl-phosphorus bonds have found numerous applications in drug development, organic materials, polymer science, and homogeneous catalysis. We describe palladium-catalyzed metathesis reactions of both compound classes, each of which proceeds through a reversible arylation manifold. The synthetic power and immediate utility of this approach are demonstrated in several applications that would be challenging to achieve by means of traditional cross-coupling methods. The C(sp(2))-S bond metathesis protocol was used in the depolymerization of a commercial thermoplastic polymer and in the late-stage derivatization of a drug. The C(sp(2))-P variant led to the convenient preparation of a variety of phosphorus heterocycles, including a potential chiral ligand and fluorescent organic materials, via a ring-closing transformation.