Oxidative Amide Coupling from Functionally Diverse Alcohols and Amines Using Aerobic Copper/Nitroxyl Catalysis
作者:Paige E. Piszel、Aristidis Vasilopoulos、Shannon S. Stahl
DOI:10.1002/anie.201906130
日期:2019.8.26
The aerobic Cu/ABNO catalyzed oxidative coupling of alcohols and amines is highlighted in the synthesis of amide bonds in diverse drug-like molecules (ABNO=9-azabicyclo[3.3.1]nonane N-oxyl). The robust method leverages the privileged reactivity of alcohols bearing electronegative hetero- atoms (O, F, N, Cl) in the β-position. The reaction tolerates over 20 unique functional groups and is demonstrated
醇和胺的需氧Cu / ABNO催化的醇和胺的氧化偶联在不同药物样分子(ABNO = 9-氮杂双环[3.3.1]壬烷N-氧基)中酰胺键的合成中得到了强调。稳健的方法利用了在β位带有负电性杂原子(O,F,N,Cl)的醇的特权反应性。该反应可耐受20多个独特的官能团,并在空气中以15 mmol的规模进行了证明。催化剂的立体约束使得在仲胺存在下伯胺的化学选择性酰胺化成为可能。所有催化剂组分都是可商购的,并且反应在温和的条件下进行,并且在两个反应伙伴中都保留了立构中心,而仅产生副产物水。