Multi-Ferrocenyl Aryl Ethers - Applying Nucleophilic Aromatic Substitution Reactions to Aryl Fluorides

Nucleophilic aromatic substitution on aryl-amido ligands promoted by oxidizing osmium(IV) centers.

Addition of amine nucleophiles to acetonitrile solutions of the OsIV anilido complex TpOs(NHPh)Cl2 (1) [Tp = hydrotris(1-pyrazolyl)borate] gives products with derivatized anilido ligands, i.e., TpOs[NH-p-C6H4(N(CH2)5)]Cl2 (2) from piperidine and TpOs[NH-p-C6H4N(CH2)4]Cl2 (3) from pyrrolidine. These materials are formed in approximately 30% yield under anaerobic conditions, together with approxi...

Efficient synthesis of 5-substituted 2-aryl-6-cyanoindolizines via nucleophilic substitution reactions

2-Aryl-6-cyano-7-methyl-5-indolizinones were successfully converted into 2-aryl-5-chloro-6-cyano-7-methylindolizines. The obtained 5-chloroindolizines readily underwent nucleophilic substitution at position 5 leading in high yields to novel 5-functionalised indolizines.

Efficient synthesis of aryl fluorides.

Selective functionalization reactions of aromatic and heteroaromatic halides with carbon, oxygen, and nitrogen nucleophiles have attracted much attention in the last decades. In addition to typical metal-catalyzed coupling reactions, direct functionalization of aryl halides through the formation of Grignard reagents offer new ways for the efficient construction of biologically interesting carbo...

Nucleophilic Substitution Reactions of Aryl Thiophene-2-carbodithioates with Pyridines in Acetonitrile

The kinetics of reactions between Z-aryl thiophene-2-carbodithioates and X-pyridines in acetonitrile at 60.0 C have been investigated. The Brönsted plots obtained for the pyridinolysis of aryl thiophene-2-carbodithioates are curved, with the center of curvature at pKa ~ 5.2 (pKa). The Brönsted plots for these nucleophilic reactions show a change in slope from a large (βX ≅ 0.78-0.87) to a small...

Modern Nucleophilic Aromatic Substitution