87170-05-6Relevant academic research and scientific papers
Terminal-Selective Functionalization of Alkyl Chains by Regioconvergent Cross-Coupling
Dupuy, Stéphanie,Zhang, Ke-Feng,Goutierre, Anne-Sophie,Baudoin, Olivier
supporting information, p. 14793 - 14797 (2016/11/23)
Hydrocarbons are still the most important precursors of functionalized organic molecules, which has stirred interest in the discovery of new C?H bond functionalization methods. We describe herein a new step-economical approach that enables C?C bonds to be constructed at the terminal position of linear alkanes. First, we show that secondary alkyl bromides can undergo in situ conversion into alkyl zinc bromides and regioconvergent Negishi coupling with aryl or alkenyl triflates. The use of a suitable phosphine ligand favoring Pd migration enabled the selective formation of the linear cross-coupling product. Subsequently, mixtures of secondary alkyl bromides were prepared from linear alkanes by standard bromination, and regioconvergent cross-coupling then provided access to the corresponding linear arylation product in only two steps.
REGIOSELECTIVE PARA-CHLORINATION OF ALKYLBENZENES ON CHEMICALLY-MODIFIED SILICA SURFACES
Konishi, Hisatoshi,Yokota, Kiyoshi,Ichihashi, Yuji,Okano, Tamon,Kiji, Jitsuo
, p. 1423 - 1426 (2007/10/02)
Chlorination of alkylbenzenes was carried out with chlorine in carbon tetrachloride in the presence of chemically-modified silica catalysts.The para/ortho ratios were remarkably higher than those obtained in the FeCl3-catalyzed chlorination. t-Butylbenzene was chlorinated at para-position almost exclusively.The catalyst could be reused several times.
