Publication: Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide
Issued Date
2017-11-16
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14645416
00404020
00404020
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2-s2.0-85030851896
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Mahidol University
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SCOPUS
Bibliographic Citation
Tetrahedron. Vol.73, No.46 (2017), 6564-6572
Suggested Citation
Pakorn Bovonsombat, Pattaradra Teecomegaet, Panisanun Kulvaranon, Aditi Pandey, Kittithorn Chobtumskul, Sireethorn Tungsirisurp, Punyanuch Sophanpanichkul, Satreerat Losuwanakul, Dechathon Soimaneewan, Patcharida Kanjanwongpaisan, Pornpawit Siricharoensang, Sirirat Choosakoonkriang Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide. Tetrahedron. Vol.73, No.46 (2017), 6564-6572. doi:10.1016/j.tet.2017.10.005 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/41666
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Title
Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide
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Abstract
© 2017 Elsevier Ltd Regioselective monobromination of various aromatics was achieved at room temperature using N-bromosuccinimide and 5 mol% of thioamides in acetonitrile. With thiourea as catalyst, activated aromatics, such as anisole, acetanilide, benzamide and phenol analogues containing electron donating or withdrawing groups, were brominated with high regioselectivity. Room temperature brominations of weakly activated aromatics and deactivated 9-fluorenone were accomplished by 5 mol% thioacetamide, higher substrates concentrations and longer reaction times. A backbonding of the bromine lone pairs with the π*of C[dbnd]S group and a halogen bond between the halogen bond donor bromine and the halogen bond acceptor sulfur of the thioamide are thought to be the principal interactions and cause of N-bromosuccinimide activation.