Copper(I)‐Catalyzed Amination of Halogenopyridines with Polyamines. Issue 1 (January 2015)

• Record Type: Journal Article
• Authors: Anokhin, Maksim V.; Averin, Alexei D.; Panchenko, Svetlana P.; Maloshitskaya, Olga A.; Buryak, Alexei K.; Beletskaya, Irina P.
• Is Part Of: Helvetica chimica acta. Volume 98:Issue 1(2015:Jan.)
• Page Start: 47
• Page End: 59
• Publication Date: 2015-01
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201400092
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Cu^I‐Catalyzed amination of 2‐bromo‐, and 2‐, 3‐, and 4‐iodopyridines with tri‐ and tetraamines aimed at the synthesis of <italic>N</italic>, <italic>N′</italic>‐diheteroaryl derivatives was studied. A strong dependence of the product yields on the nature of starting compounds and the ligand used was observed. The increase in the number of ethene‐1, 2‐diamine fragments in the polyamine structure led to the increase in the yields of polyheteroarylated compounds, whereas propane‐1, 3‐diamine fragments favored the formation of monopyridinyl derivatives and promoted the heteroarylation of the secondary amino groups. 2‐Iodopyridine, as a more reactive compound, readily formed <italic>N</italic>, <italic>N</italic>‐diarylated products. The best yields of the target <italic>N</italic>, <italic>N′</italic>‐dipyridin‐2‐yl derivatives were 76% in the case of the triamine and 68% in the case of the tetraamine. A comparison of Cu^I‐ and Pd⁰‐mediated heteroarylation of polyamines was also presented.</p> </abstract>