Regioselective Metal‐Free C2−H Arylation of Quinoline N‐Oxides with Aryldiazonium Salts/Anilines under Ambient Conditions. Issue 8 (22nd June 2017)

• Record Type: Journal Article
• Authors: Kumar, Rakesh; Kumar, Rakesh; Dhiman, Ankit Kumar; Sharma, Upendra
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 8(2017)
• Page Start: 1043
• Page End: 1053
• Publication Date: 2017-06-22
• Subjects: arylation -- C−H functionalization -- quinolines -- regioselectivity -- synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700267
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Herein, a base‐promoted direct C2−H arylation of quinoline N ‐oxides with aryldiazonium salts under metal‐free conditions is reported. This reaction avoids the need for an oxidant, metal catalyst, or inert atmosphere and proceeds through a highly regioselective C−H bond functionalization to provide a series of C2‐arylated quinoline N ‐oxides. Abundantly available amines (anilines and heteroaryl amines) can also be employed as arylating agents through an in situ diazotization process, thereby affording a library of diverse 2‐arylquinoline N ‐oxides in moderate‐to‐good yields. The synthesized 2‐arylated quinoline N ‐oxides were further converted into C8‐substituted quinolines to demonstrate the applicability of this catalytic approach. A radical pathway is proposed for the C2 arylation, based on a preliminary mechanistic study. Abstract : I′ll C2 it : A base‐promoted direct C2−H arylation of quinoline N ‐oxides with aryldiazonium salts under metal‐free conditions has been developed that provides access to a series of C2‐arylated quinoline N ‐oxides.