These amines should actually serve as assisting bases, because of their low nucleophilicity.
Matthias Gabler, Manfred Schubert-Zsilavecz 2011, 'Tertiary Alkylamines as Nucleophiles in Substitution Reactions at Heteroaromatic HalideDuring the Synthesis of the Highly Potent Pirinixic Acid Derivative 2-(4-Chloro-6-(2,3-dimethylphenylamino)pyrimidin-2-ylthio)octanoicAcid (YS-121)', Moleculeshttp://www.mdpi.com/1420-3049/16/12/10013/. Retrieved from DOAJ CC BY 4.0 (https://creativecommons.org/licenses/by-sa/4.0/legalcode)
The sensitivities to solvent nucleophilicity and solvent ionizing power are compared to values available for other substrates.
Dennis N. Kevill, Stacey L. Mlynarski, Lamia Yaakoubd, Malcolm J. D’Souza 2008, 'Concerted Solvent Processes for Common Sulfonyl Chloride Precursors used in the Synthesisof Sulfonamide-based Drugs', International Journal of Molecular Scienceshttp://www.mdpi.com/1422-0067/9/5/914/. Retrieved from DOAJ CC BY 4.0 (https://creativecommons.org/licenses/by-sa/4.0/legalcode)
The formation of these two types of reaction products depends on the nucleophilicity of the arene.
Dmitry S. Ryabukhin, Dmitry N. Zakusilo, Mikhail O. Kompanets, Anton A.Tarakanov,Irina A. Boyarskaya, Tatiana O. Artamonova, Mikhail A. Khohodorkovskiy, Iosyp O. Opeida,Aleksander V. Vasilyev 2016, 'Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organicsynthesis based on biomass-derived products', Beilstein Journal of Organic Chemistryhttps://doi.org/10.3762/bjoc.12.202. Retrieved from DOAJ CC BY 4.0 (https://creativecommons.org/licenses/by-sa/4.0/legalcode)
The selectivity seems to be controlled by the nucleophilicity of double bonds and by stereoelectronic and steric effects.
Giuseppe Trusso Sfrazzetto, Gaetano A. Tomaselli, Rosa M. Toscano, Francesco P. Ballistreri,Andrea Pappalardo, Maria E. Amato 2013, 'Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediatedby Methyltrioxorhenium', Moleculeshttp://www.mdpi.com/1420-3049/18/11/13754. Retrieved from DOAJ CC BY 4.0 (https://creativecommons.org/licenses/by-sa/4.0/legalcode)