Effective BI‐DIME Ligand for Suzuki–Miyaura Cross‐Coupling Reactions in Water with 500 ppm Palladium Loading and Triton X,Asian Journal of Organic Chemistry

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Effective BI‐DIME Ligand for Suzuki–Miyaura Cross‐Coupling Reactions in Water with 500 ppm Palladium Loading and Triton X
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2017-05-04 , DOI: 10.1002/ajoc.201700137
Nitinchandra D. Patel ₁ , Daniel Rivalti ₁ , Frederic G. Buono ₁ , Arindom Chatterjee ₁ , Bo Qu ₁ , Stefan Braith ₁ , Jean-Nicolas Desrosiers ₁ , Sonia Rodriguez ₁ , Joshua D. Sieber ₁ , Nizar Haddad ₁ , Keith R. Fandrick ₁ , Heewon Lee ₁ , Nathan K. Yee ₁ , Carl A. Busacca ₁ , Chris H. Senanayake ₁

Affiliation

An efficient, sustainable, and broadly applicable procedure has been developed for Suzuki–Miyaura cross‐coupling reactions in environmentally benign solvent (water) by employing as little as 500 ppm Pd(OAc)₂ with a monophosphorus BI‐DIME ligand in the presence of inexpensive and commercially available nonionic surfactant Triton X‐100. This method was applied to a broad range of functionalized reaction partners, thereby affording excellent yields of the coupling products, including active pharmaceutical ingredients (APIs). An interesting kinetic study by using reaction calorimetry is also presented, which describes the effect of reaction parameters that enabled the low catalyst loading.

中文翻译：

钯载量和Triton X的水中Suzuki–Miyaura交叉偶联反应的有效BI‐DIME配体

对于在环境良性溶剂（水）中的Suzuki-Miyaura交叉偶联反应，已经开发出一种有效，可持续且广泛适用的程序，方法是在存在以下条件的情况下，通过单磷BI-DIME配体使用低至500 ppm的Pd（OAc）₂廉价且可商购的非离子表面活性剂Triton X-100。该方法被应用于各种功能化的反应伙伴，从而提供了包括活性药物成分（API）在内的偶联产物的优异收率。还介绍了使用反应量热法进行的有趣的动力学研究，该研究描述了反应参数的影响，使催化剂负载量较低。

更新日期：2017-05-04

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