FeCl<sub>3</sub>·6H<sub>2</sub>O as a Mild Catalyst for Nucleophilic Substitution of Symmetrical Bis(indoyl)methanes
Chayamon Chantana, Jaray Jaratjaroonphong
Abstract
In this paper, unsymmetrical bis(indolyl)methane (BIM) and 3-alkylindole derivatives are smoothly synthesized from symmetrical BIMs with a variety of nucleophiles including heteroaromatic/aromatic compounds, allylsilane and alkynylsilane. FeCl3·6H2O is found to be a mild and highly effective catalyst for this nucleophilic substitution reaction in which N-methyl-2-phenylindole behaves as a good leaving group in the Csp3–Csp2 bond cleavage reaction. The operational ease, nonexpensive and environmentally friendly catalyst, mild reaction conditions, broad functional group tolerance, and scalability of this reaction strategy are advantages of the present procedure.
Topics & Concepts
ChemistryCatalysisNucleophileNucleophilic substitutionMedicinal chemistryReaction conditionsSubstitution reactionBond cleavageFunctional groupNucleophilic additionOrganic chemistryNucleophilic aromatic substitutionCombinatorial chemistryPolymerSynthesis of Indole DerivativesChemical Synthesis and ReactionsAxial and Atropisomeric Chirality Synthesis