Suzuki‐Miyaura Cross‐Coupling of Amides using Well‐Defined, Air‐Stable [(PR 3 ) 2 Pd(II)X 2 ] Precatalysts
Suzuki‐Miyaura Cross‐Coupling of Amides using Well‐Defined, Air‐Stable [(PR 3 ) 2 Pd(II)X 2 ] Precatalysts
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DOI：
10.1002/adsc.202000122
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发表时间：
2020-04
影响因子：
5.4
通讯作者：
Siyue Ma;Tongliang Zhou;Guangchen Li;M. Szostak
中科院分区：
文献类型：
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作者：
Siyue Ma;Tongliang Zhou;Guangchen Li;M. Szostak
报道了一种使用高活性、高稳定性和空气稳定的Pd−膦预催化剂的铃木-宫浦交叉偶联酰胺的通用方法。最值得注意的是，该方法代表了在新兴的酰胺键交叉偶联歧管中使用实用和操作简单的Pd(II)−膦预催化剂的第一个例子。反应在负载量为0.10 摩尔%时是有效的，为N-−-C(O)键断裂提供了高化学选择性的联芳基酮。这种多用途的方法首次实现了Pd-−膦催化的Pd-ppm负载的酰胺的交叉偶联。这种C-−-N交叉偶联可以通过Pd催化的正交交叉偶联有效地制备医药中间体。我们完全期待操作简单的[(Pr3)2Pd(II)X2]预催化剂作为N-−-C(O)交叉偶联的有效触发剂将具有广泛的合成和催化兴趣。
A versatile method for the Suzuki‐Miyaura cross‐coupling of amides using highly active, well‐defined, and air‐stable Pd−phosphine precatalysts is reported. Most notably, the method represents the first example of using practical and operationally‐simple Pd(II)−phosphine precatalysts in the emerging amide bond cross‐coupling manifold. The reactions are efficient at 0.10 mol% loading, furnishing biaryl ketones with high chemoselectivity for N−C(O) bond cleavage. This versatile method enables for the first time to achieve Pd−phosphine‐catalyzed cross‐coupling of amides at ppm loading. This C−N cross‐coupling can be used to efficiently furnish pharmaceutical intermediates by orthogonal Pd‐catalyzed cross‐couplings. We fully expect that operationally‐simple [(PR3)2Pd(II)X2] precatalysts as effective triggers for N−C(O) cross‐coupling will be of broad synthetic and catalytic interest.