Chan−Lam Arylation of Benzimidazole and its Derivatives in the Presence of Copper‐Containing Minerals. Issue 4 (26th January 2021)

• Record Type: Journal Article
• Authors: Györke, Gábor; Dancsó, András; Volk, Balázs; Milen, Mátyás
• Is Part Of: ChemistrySelect. Volume 6:Issue 4(2021)
• Page Start: 802
• Page End: 807
• Publication Date: 2021-01-26
• Subjects: Catalysis -- Chan−Lam reaction -- Copper-Containing Minerals -- Economical Procedure -- N-Arylation; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202004596
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Copper catalysis plays a remarkable role in synthetic organic chemistry. The catalytic activity of copper‐containing minerals is not sufficiently presented in the literature, even though the economical value of such procedures is rather high. With the direct usage of these readily available ores, the highly polluting industrial copper production can be avoided. In the present work, the copper‐containing mineral catalyzed Chan−Lam reaction of benzimidazole, substituted benzimidazoles or imidazole with various phenylboronic acids is described. A total of nine readily available ores were tested in our model reaction with bornite (Cu5 FeS4 ) and chalcocite (Cu2 S) being the best among them. The in situ formed catalytic system of Cu5 FeS4 /TMEDA was able to produce the desired products in up to 98 % yields and it was reusable making this process even more economical and environmentally friendly. Abstract : Chan−Lam coupling of arylboronic acids and benzimidazole, its derivatives or imidazole was studied with nine readily available copper‐containing minerals and with a wide variety of substrates. The reaction was best performed with bornite and chalcocite in the presence of TMEDA, at room temperature. The desired N ‐arylated products could be isolated with up to 98 % yield.