Activation of alkyl halides via a silver-catalyzed carbene insertion process

H V Rasika Dias; R Greg Browning; Sharon A Polach; Himashinie V K Diyabalanage; Carl J Lovely

doi:10.1021/ja034801o

Activation of alkyl halides via a silver-catalyzed carbene insertion process

J Am Chem Soc. 2003 Aug 6;125(31):9270-1. doi: 10.1021/ja034801o.

Authors

H V Rasika Dias¹, R Greg Browning, Sharon A Polach, Himashinie V K Diyabalanage, Carl J Lovely

Affiliation

¹ Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, USA. dias@uta.edu

PMID: 12889937
DOI: 10.1021/ja034801o

Abstract

The silver complex [HB(3,5-(CF3)2Pz)3]Ag(THF) featuring a highly fluorinated tris(pyrazolyl)borate ligand catalyzes the formation of aliphatic carbon-halogen bond activation products under remarkably mild conditions. For example, the reaction between CHCl3 and ethyl diazoacetate (EDA) at room temperature in the presence of the silver catalyst afforded HClC(CO2Et)CCl2H in 60% yield. The presence of beta-hydrogens on the alkyl halide leads to net hydrogen halide addition to the carbene and an alkene.