Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA.
Org Biomol Chem. 2018 Nov 7;16(43):7998-8010. doi: 10.1039/c8ob01832d.
Cross-coupling reactions are among the most powerful C-C and C-X bond forming tools in organic chemistry. Traditionally, cross-coupling methods rely on the use of aryl halides or pseudohalides as electrophiles. In the past three years, decarbonylative cross-couplings of amides have emerged as an attractive method for the construction of a wide variety of carbon-carbon and carbon-heteroatom bonds, allowing for the synthetically-valuable functional group inter-conversion of the amide bond. These previously elusive reactions hinge upon selective activation of the N-C(O) acyl amide bond, followed by CO extrusion, in a formal double N-C/C-C bond activation, to generate a versatile aryl-metal intermediate as an attractive alternative to traditional cross-couplings of aryl halides and pseudohalides. In this perspective review, we present recent advances and key developments in the field of decarbonylative cross-coupling reactions of amides as well as discuss future challenges and potential applications for this exciting field.
交叉偶联反应是有机化学中最强大的 C-C 和 C-X 键形成工具之一。传统上，交叉偶联方法依赖于芳基卤化物或拟卤化物作为亲电试剂。在过去的三年中，酰胺的脱羰交叉偶联已成为构建各种碳-碳和碳-杂原子键的一种有吸引力的方法，允许酰胺键的合成上有价值的官能团转化。这些以前难以捉摸的反应取决于对 N-C(O)酰基酰胺键的选择性活化，然后是 CO 逐出，在形式上的双重 N-C/C-C 键活化中，生成一种多功能的芳基金属中间体，作为传统芳基卤化物和拟卤化物交叉偶联的有吸引力的替代物。在这篇观点综述中，我们介绍了酰胺脱羰交叉偶联反应领域的最新进展和关键发展，并讨论了该令人兴奋的领域的未来挑战和潜在应用。
