Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Org Lett. 2013 Jul 5;15(13):3440-3. doi: 10.1021/ol4015078. Epub 2013 Jun 20.
A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed γ-C(sp(3))-H arylation, metal-free ε-C(sp(2))-H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.
本文报道了一种通过远程 C-H 键的顺序官能化来合成四氢喹啉（THQs）的新策略。该方法使用单个吡啶甲酰胺导向/保护基来实现 Pd 催化的γ-C(sp(3))-H 芳基化、无金属的ε-C(sp(2))-H 碘化以及 Cu 催化的分子内 C-N 交叉偶联。该反应序列高效且多功能，可从易得的芳基碘化物和脂肪族胺前体制备具有复杂取代模式的 THQs。
