Domino Cu-catalyzed C-N coupling/hydroamidation:: A highly efficient synthesis of nitrogen heterocycles
Domino Cu-catalyzed C-N coupling/hydroamidation:: A highly efficient synthesis of nitrogen heterocycles
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DOI：
10.1002/anie.200602917
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发表时间：
2006-01-01
影响因子：
16.6
通讯作者：
Buchwald, Stephen L.
中科院分区：
文献类型：
--
作者：
Martin, Ruben;Rivero, Marta Rodriguez;Buchwald, Stephen L.
杂环化合物具有重要的化学和生物学意义。[1]特别是，含氮杂环是许多生物活性天然产物、医学上重要的化合物和有机材料的结构成分。[2]最近的策略为基础的金属催化反应的杂环化合物的合成很好地补充了经典的合成方法。它们的优点之一是经常避免苛刻的条件，并且可以利用容易获得的起始材料。[3]尽管取得了进展，但需要更灵活和通用的路线来获得各种杂环。特别是，能够容易地获得具有不同且易于操作的取代基的杂环核的技术仍然至关重要。在过去的十年中，金属催化的C3 N键形成反应[4]已经成为学术和制药实验室制备含氮化合物的重要方法。[5]近年来，Cu促进的过程已经发展成为更广泛实践的Pd催化反应的可行替代方案。[6，7]铜基方法的特点是范围广，效率高，反应条件温和，因此使其成为进一步应用的有吸引力的载体。[8]开发一种用于从共同的结构单元产生多个类别的含氮杂环的方法是非常期望的目标。在此之前，Ackermann证明了Cacchi吲哚合成[9]的底物可以通过Pd或Cu催化的α-炔基芳基卤化物的胺化来制备。[10]在这些偶联方法的条件下，以有效的方式环化成N-苄基或N-芳基吲哚。[11]我们想知道是否有可能实现相关的转化作为获得其他重要的氮杂环的手段，
Heterocyclic compounds are of great chemical and biological significance.[1] In particular, nitrogen-containing heterocycles are structural constituents of many bioactive natural products, medicinally important compounds, and organic materials.[2] Recent strategies for the synthesis of heterocycles based on metal-catalyzed reactions nicely complement the classical synthetic approaches. Among their advantages is that harsh conditions are frequently avoided and readily available starting materials can be utilized.[3] Despite the advances realized, more flexible and general routes to a variety of heterocycles are needed. In particular, techniques that can readily give access to heterocyclic cores with a diverse and easily manipulated set of substituents are still of critical importance.In the last decade, metal-catalyzed CÀN bond-forming reactions [4] have become important methods for the preparation of nitrogen-containing compounds in both academic and pharmaceutical laboratories.[5] In recent years, Cu-promoted processes have evolved into viable alternatives to the more widely practiced Pd-catalyzed reactions.[6, 7] The Cu-based methods are distinguished by their broad scope, high efficiency, and mild reaction conditions, thus making them attractive vehicles for further applications.[8] The development of a method for generating multiple classes of nitrogen-containing heterocycles from common building blocks is a highly desirable goal. Previously, Ackermann showed that substrates for the Cacchi indole synthesis [9] can be prepared by Pd-or Cu-catalyzed amination of oalkynyl aryl halides.[10] Under the conditions of these coupling processes, cyclization to the N-benzyl or N-aryl indoles takes place in an efficient manner.[11] We wondered whether it would be possible to effect a related transformation as a means to access other important nitrogen heterocycles,