A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.
A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.
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DOI：
10.1021/ja1073799
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发表时间：
2010-10-13
影响因子：
15
通讯作者：
Buchwald SL
中科院分区：
文献类型：
--
作者：
Kinzel T;Zhang Y;Buchwald SL
在碱性条件下快速脱硼的硼酸，如多氟苯基硼酸和五元2-杂芳族硼酸，是Suzuki-Miyaura反应的特别具有挑战性的偶联配偶体。然而，能够使用这些基底对于许多应用是非常期望的。已经发现单齿联芳基膦配体可以促进这些偶联过程，我们开发了在硼酸分解缓慢的条件下形成催化活性物质的预催化剂。使用这种预催化剂，广泛的（杂）芳基氯化物、溴化物和三氟甲磺酸酯与多氟苯基、2-呋喃、2-噻吩和2-吡咯硼酸及其类似物的Suzuki-Miyaura反应在室温或40 °C下在短的反应时间内进行，以优异的产率得到所需的产物。
Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and five-membered 2-heteroaromatic boronic acids, are especially challenging coupling partners for Suzuki-Miyaura reactions. Nevertheless, being able to use these substrates is highly desirable for a number of applications. Having found that monodentate biarylphosphine ligands can promote these coupling processes, we developed a precatalyst that forms the catalytically active species under conditions where boronic acid decomposition is slow. With this precatalyst, Suzuki-Miyaura reactions of a wide range of (hetero)aryl chlorides, bromides, and triflates with polyfluorophenyl, 2-furan, 2-thiophene and 2-pyrroleboronic acids and their analogs proceed at room temperature or 40 °C in short reaction times to give the desired products in excellent yields.
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影响因子：
15
作者：
Knapp DM;Gillis EP;Burke MD
通讯作者：
Burke MD
影响因子：
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作者：
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15
作者：
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通讯作者：
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