One‐Pot Synthesis and Applications of N‐Heteroaryl Iodonium Salts

ChemistryOpen

Dr. Marcin Bielawski¹  Joel Malmgren¹  Dr. Leticia M. Pardo¹  Ylva Wikmark¹ 

[1] Department of Organic Chemistry, Stockholm University, 106 91 Stockholm (Sweden)

关键词: arylation;    heterocycles;    hypervalent iodine;    iodonium salts;    oxidation;   

DOI  :  10.1002/open.201300042

来源: Wiley

【 摘 要 】

Abstract

An efficient one-pot synthesis of N-heteroaryl iodonium triflates from the corresponding N-heteroaryl iodide and arene has been developed. The reaction conditions resemble our previous one-pot syntheses, with suitable modifications to allow N-heteroaryl groups. The reaction time is only 30 min, and no anion exchange is required. The obtained iodonium salts were isolated in a protonated form, these salts can either be employed directly in applications or be deprotonated prior to use. The aryl groups were chosen to induce chemoselective transfer of the heteroaryl moiety to various nucleophiles. The reactivity and chemoselectivity of these iodonium salts were demonstrated by selectively introducing a pyridyl moiety onto both oxygen and carbon nucleophiles in good yields.

【 授权许可】

CC BY-NC   
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Creative Commons Attribution-NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.