Ratushnyy Maxim, Kvasovs Nikita, Sarkar Sumon, Gevorgyan Vladimir
Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, IL, 60607-7061, USA.
Department of Chemistry and Biochemistry, University of Texas at Dallas, 800 West Campbell, BSB13, Richardson, TX, 75080, USA.
Angew Chem Int Ed Engl. 2020 Jun 22;59(26):10316-10320. doi: 10.1002/anie.201915962. Epub 2020 Apr 6.
A mild visible-light-induced Pd-catalyzed intramolecular C-H arylation of amides is reported. The method operates by cleavage of a C(sp )-O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-catalyzed conditions.
报道了一种温和的可见光诱导的钯催化酰胺分子内C-H芳基化反应。该方法通过C(sp)-O键的断裂来进行，生成杂化芳基钯自由基中间体。随后的1,5-氢原子迁移、分子内环化和再芳构化步骤生成了有价值的羟吲哚和异吲哚啉-1-酮结构单元。值得注意的是，该方法能够得到含有易烯醇化官能团的产物，而这些官能团与传统钯催化条件不相容。
