Jump to main content
Jump to site search

Issue 32, 2016
Previous Article Next Article

Pd-catalyzed divergent trifluoroethylation and arylation of arylboronic acids by aryl(2,2,2-trifluoroethyl)iodonium triflates

Author affiliations

Abstract

Highly electrophilic aryl(2,2,2-trifluoroethyl)iodonium triflates have been used for the first time as trifluoroethyl and aryl transfer reagents in Pd-catalyzed functionalization of arylboronic acids. Electron-rich arylboronic acids reacted with aryl(2,2,2-trifluoroethyl)iodonium triflates (2a–b) in CH3CN in the presence of Pd2(dba)3 and K3PO4 at room temperature to provide trifluoroethyl arenes in up to 82% yield, while the reactions of both electron-rich and -poor arylboronic acids with 2a–b in DMF in the presence of Pd[P(t-Bu)3]2 and Cs2CO3 at 40 °C afforded arylation products in up to 99% yield. This tunable protocol allows access to trifluoroethyl arenes or biaryls in good to excellent yields under mild conditions and without the addition of extra ligands.

Graphical abstract: Pd-catalyzed divergent trifluoroethylation and arylation of arylboronic acids by aryl(2,2,2-trifluoroethyl)iodonium triflates

Back to tab navigation

Supplementary files

Publication details

The article was received on 10 Jun 2016, accepted on 28 Jun 2016 and first published on 28 Jun 2016


Article type: Paper
DOI: 10.1039/C6OB01384H
Org. Biomol. Chem., 2016,14, 7654-7658

  •   Request permissions

    Pd-catalyzed divergent trifluoroethylation and arylation of arylboronic acids by aryl(2,2,2-trifluoroethyl)iodonium triflates

    J. Yang, Q. Han, C. Zhao, T. Dong, Z. Hou, H. Qin and C. Zhang, Org. Biomol. Chem., 2016, 14, 7654
    DOI: 10.1039/C6OB01384H

Search articles by author

Spotlight

Advertisements