Pakorn BovonsombatPunyanuch SophanpanichkulAditi PandeySireethorn TungsirisurpPacharasak LimthavornlitKittithorn ChobtumskulPunn KuhataparukSuthapat SathityatiwatPattaradra TeecomegaetMahidol University2018-11-232018-11-232015-04-22Tetrahedron Letters. Vol.56, No.17 (2015), 2193-219618733581004040392-s2.0-84939986504https://repository.li.mahidol.ac.th/handle/20.500.14594/35467© 2015 Elsevier Ltd. All rights reserved. Abstract A metal and acid-free electrophilic aromatic chlorination methodology involving catalytic thiourea activation of N-chlorosuccinimide (NCS) is reported herein. Moderate yields and regioselectivities of chlorinated aromatics were obtained using a combination of 1.05-1.15 equiv of NCS and 5 mol % of thiourea at room temperature in acetonitrile. A halogen bond between the sulfur atom of thiourea and the sigma-hole of the NCS chlorine atom is thought to enhance the electrophilic activity of the chlorine of NCS.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryArticleSCOPUS10.1016/j.tetlet.2015.03.034