Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.
Chem Asian J. 2018 Sep 4;13(17):2499-2504. doi: 10.1002/asia.201800441. Epub 2018 Jun 10.
An efficient divergent functionalization of N-alkylated ortho-alkenylanilines to substituted indoles and quinolines has been accomplished by employing rhodium-catalyzed cross-dehydrogenative coupling and silver-mediated oxidative cyclization, respectively. The developed methods tolerate various functional groups and allow the synthesis of substituted indoles and quinolines in good to excellent yield. Synthetic utility is demonstrated through conversion to an indole with antimicrobial activity and C-H bond functionalization of 2-arylquinolines. Furthermore, a plausible mechanism was proposed based on preliminary mechanistic investigations.
通过采用铑催化的交叉脱氢偶联和银介导的氧化环化反应，分别实现了 N-烷基化邻烯基苯胺的高效发散官能化，得到取代的吲哚和喹啉。所开发的方法耐受各种官能团，并允许以良好至优异的产率合成取代的吲哚和喹啉。通过转化为具有抗菌活性的吲哚和 2-芳基喹啉的 C-H 键官能化，展示了合成的实用性。此外，根据初步的机理研究提出了一个合理的机理。
