Efficient copper-catalyzed trifluoromethylation of aromatic and heteroaromatic iodides: the beneficial anchoring effect of borates

Zsombor Gonda; Szabolcs Kovács; Csaba Wéber; Tamás Gáti; Attila Mészáros; András Kotschy; Zoltán Novák

doi:10.1021/ol501967c

Efficient copper-catalyzed trifluoromethylation of aromatic and heteroaromatic iodides: the beneficial anchoring effect of borates

Org Lett. 2014 Aug 15;16(16):4268-71. doi: 10.1021/ol501967c. Epub 2014 Jul 28.

Authors

Zsombor Gonda¹, Szabolcs Kovács, Csaba Wéber, Tamás Gáti, Attila Mészáros, András Kotschy, Zoltán Novák

Affiliation

¹ MTA-ELTE "Lendület" Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös Loránd University , Pázmány Péter stny. 1/a, H-1117 Budapest, Hungary.

PMID: 25068681
DOI: 10.1021/ol501967c

Abstract

Efficient copper-catalyzed trifluoromethylation of aromatic iodides was achieved with TMSCF3 in the presence of trimethylborate. The Lewis acid was used to anchor the in situ generated trifluoromethyl anion and suppress its rapid decomposition. Broad applicability of the new trifluoromethylating reaction was demonstrated in the functionalization of different aromatic and heteroaromatic iodides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Borates / chemistry
Borates / pharmacology*
Catalysis
Copper / chemistry*
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry*
Hydrocarbons, Iodinated / chemistry*
Methylation
Molecular Structure
Silanes / chemical synthesis*
Silanes / chemistry*

Substances

Borates
Hydrocarbons, Fluorinated
Hydrocarbons, Iodinated
Silanes
Copper
trimethyl(trifluoromethyl)silane