Jordan-Hore James A, Johansson Carin C C, Beck Elizabeth M, Gaunt Matthew J
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
J Am Chem Soc. 2008 Dec 3;130(48):16184-6. doi: 10.1021/ja806543s.
We report a new Pd(II)-catalyzed C-H bond amination reaction to form carbazoles, an important motif that is prevalent in a range of systems. The catalytic amination process operates under extremely mild conditions and produces carbazole products in good to excellent yields. Carbazoles possessing complex molecular architecture can also be formed using this reaction, highlighting its potential in natural product synthesis applications. Preliminary mechanistic investigations reveal the reaction proceeds through a Pd(II)/Pd(IV) manifold and that reductive elimination from a high oxidation state Pd(IV) complex facilitates the mild conditions of this transformation.
我们报道了一种新型的钯（II）催化的C-H键胺化反应，用于形成咔唑，咔唑是一种在一系列体系中普遍存在的重要结构单元。该催化胺化过程在极其温和的条件下进行，咔唑产物的产率良好至优异。使用该反应还可以形成具有复杂分子结构的咔唑，突出了其在天然产物合成应用中的潜力。初步的机理研究表明，该反应通过钯（II）/钯（IV）机理进行，并且从高氧化态钯（IV）络合物的还原消除促进了这种转化的温和条件。
