Carbon-carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations

Tsuyuka Sugiishi; Hideki Amii; Kohsuke Aikawa; Koichi Mikami

doi:10.3762/bjoc.11.286

Carbon-carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations

Beilstein J Org Chem. 2015 Dec 18:11:2661-70. doi: 10.3762/bjoc.11.286. eCollection 2015.

Authors

Tsuyuka Sugiishi¹, Hideki Amii¹, Kohsuke Aikawa², Koichi Mikami²

Affiliations

¹ Division of Molecular Science, Faculty of Science and Technology, Gunma University, 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan.
² Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan.

Abstract

This short review highlights the copper-mediated fluoroalkylation using perfluoroalkylated carboxylic acid derivatives. Carbon-carbon bond cleavage of perfluoroalkylated carboxylic acid derivatives takes place in fluoroalkylation reactions at high temperature (150-200 °C) or under basic conditions to generate fluoroalkyl anion sources for the formation of fluoroalkylcopper species. The fluoroalkylation reactions, which proceed through decarboxylation or tetrahedral intermediates, are useful protocols for the synthesis of fluoroalkylated aromatics.

Keywords: carbon–carbon bond cleavage; decarboxylation; fluoral; tetrahedral intermediate; trifluoroacetate; trifluoromethylation; β-carbon elimination.

Publication types

Review