Copper(II) triflate-catalyzed direct arylation for synthesis of biphenyls using diaryliodonium salts as arylating reagents. Issue 37 (14th September 2016)

• Record Type: Journal Article
• Authors: Wang, Xuesong; Huang, Dayun; Wang, Xingyong; Zeng, Xiaobao; Wang, Xinyan; Hu, Yuefei
• Is Part Of: Tetrahedron letters. Volume 57:Issue 37(2016)
• Page Start: 4235
• Page End: 4238
• Publication Date: 2016-09-14
• Subjects: Copper catalyst -- Direct arylation -- Biphenyls -- Friedel–Crafts reaction -- Diaryliodonium salts; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.08.027
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An easy synthesis of biphenyls with one highly electron-rich phenyl is developed. Diaryliodonium salts are used as arylating reagents catalyzed by Cu(OTf)2 . A modified F–C pathway is proposed based on the reactivity and site-selectivity. Cu(OTf)2 is proposed as both a Lewis acid catalyst and a transition-metal catalyst. Abstract: An efficient synthesis of biphenyls was developed by a Cu(OTf)2 -catalyzed direct arylation between an electron-rich arene and a diaryliodonium salt. The reaction went through a modified Friedel–Crafts reaction mechanism, in which Cu(OTf)2 served as both Lewis-acid catalyst and transition-metal catalyst to generate the aryl carbocation from the corresponding diaryliodonium salt.