Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
J Am Chem Soc. 2010 Mar 24;132(11):3676-7. doi: 10.1021/ja100676r.
We report a conceptually new approach to the direct amination of aromatic C-H bonds. In this process, an oxime ester function reacts with an aromatic C-H bond under redox-neutral conditions to form, in the case studied, an indole product. These reactions occur with relatively low catalyst loading (1 mol %) by a mechanism that appears to involve an unusual initial oxidative addition of an N-O bond to a Pd(0) species. The Pd(II) complex from oxidative addition of the N-X bond has been isolated for the first time, and evidence for the intermediacy of such oxidative addition products in the catalytic reaction has been gained.
我们报告了一种新概念的直接芳基 C-H 键胺化方法。在这个过程中，肟酯官能团在氧化还原中性条件下与芳基 C-H 键反应，在所研究的情况下，形成吲哚产物。这些反应在相对较低的催化剂负载（1 mol%）下发生，其反应机理似乎涉及到 N-O 键的异常初始氧化加成到 Pd(0)物种上。首次分离出了 N-X 键氧化加成的 Pd(II)配合物，并获得了催化反应中存在这种氧化加成产物中间体的证据。
