Publication: Novel regioselective aromatic chlorination via catalytic thiourea activation of N-chlorosuccinimide
Issued Date
2015-04-22
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ISSN
18733581
00404039
00404039
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2-s2.0-84939986504
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Mahidol University
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SCOPUS
Bibliographic Citation
Tetrahedron Letters. Vol.56, No.17 (2015), 2193-2196
Suggested Citation
Pakorn Bovonsombat, Punyanuch Sophanpanichkul, Aditi Pandey, Sireethorn Tungsirisurp, Pacharasak Limthavornlit, Kittithorn Chobtumskul, Punn Kuhataparuk, Suthapat Sathityatiwat, Pattaradra Teecomegaet Novel regioselective aromatic chlorination via catalytic thiourea activation of N-chlorosuccinimide. Tetrahedron Letters. Vol.56, No.17 (2015), 2193-2196. doi:10.1016/j.tetlet.2015.03.034 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/35467
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Title
Novel regioselective aromatic chlorination via catalytic thiourea activation of N-chlorosuccinimide
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Abstract
© 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.
