基于固有弱配位氧基团导向的钌（II）催化2-芳基喹啉-4（1）-酮的C5官能化反应

Inherent Weakly Coordinating Oxo-Group-Directed Ruthenium(II)-Catalyzed C5 Functionalization of 2-Arylquinolin-4(1)-ones.

作者信息

Jangir Tarun, Nipate Dhananjay S, Dhyani Vani, Khichar Nikita, Rangan Krishnan, Kumar Anil

机构信息

Department of Chemistry, Birla Institute of Technology and Science, Pilani, Pilani Campus, Vidya Vihar, Pilani, Rajasthan 333031, India.

Department of Chemistry, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Kapra Mandal, Medchal District, Secunderabad, Telangana 500078, India.

出版信息

Org Lett. 2025 Aug 15;27(32):8881-8886. doi: 10.1021/acs.orglett.5c02418. Epub 2025 Aug 5.

DOI:10.1021/acs.orglett.5c02418

PMID:40762573

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12362596/

Abstract

A Ru(II)-catalyzed inherent weakly coordinating oxo-group-directed site-selective C5 functionalization of 2-arylquinolin-4(1)-ones using various coupling partners like allyl alcohols, acrylates, styrenes, maleimides, and acrylamide has been described. The developed method allowed the synthesis of C5-substituted 2-arylquinolin-4(1)-ones in good to excellent yields. The protocol is compatible with a broad range of functional groups and can be used on the gram scale. In addition, based on the control experiments, a plausible reaction mechanism has been proposed for this transformation.

摘要

已报道了一种铑（II）催化的、利用烯丙醇、丙烯酸酯、苯乙烯、马来酰亚胺和丙烯酰胺等各种偶联伙伴对2-芳基喹啉-4（1）-酮进行固有弱配位氧代基团导向的位点选择性C5官能化反应。所开发的方法能够以良好至优异的产率合成C5取代的2-芳基喹啉-4（1）-酮。该方案与广泛的官能团兼容，可用于克级规模。此外，基于对照实验，还为这种转化提出了一种合理的反应机理。