Iron-catalyzed cross-coupling of heteroaromatic tosylates with alkyl and aryl Grignard reagents

• Published in: Applied organometallic chemistry Vol. 29; no. 5; pp. 296 - 300
• Main Authors: Chen, Xu, Quan, Zheng-Jun, Wang, Xi-Cun
• Format: Journal Article
• Language: English
• Published: Blackwell Publishing Ltd 01.05.2015
• Subjects: Aromatic compounds; cross-coupling; Derivatives; Grignard reagents; heteroaromatic sulfonates; Ligands; Metalorganic compounds; Pyridines; pyrimidine derivatives; Pyrimidines; Reaction time
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.3289

An Fe(III)‐catalyzed cross‐coupling of N‐heteroaromatic tosylates with aryl and alkyl Grignard reagents is presented. The reaction proceeds at −20°C to room temperature with short reaction time (15–30 min.), and the corresponding products are obtained with moderate to high yields. In particular, low‐cost and abundantly available FeCl3 or Fe(acetylacetonate)3 catalyze the reaction without other special ligands. All tested N‐heteroaromatic tosylates that are available including pyridine and pyrimidine derivatives were subject to the reaction, resulting in the expected products. Copyright © 2015 John Wiley & Sons, Ltd. Fe(III)‐catalyzed cross‐coupling of N‐heteroaromatic tosylates with aryl and alkyl Grignard reagents is presented. The cross‐coupling was catalyzed by FeCl3 or Fe(acac)3/TMEDA at −20°C to room temperature with short reaction times (15–30 min).