Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl2 and NH4SCN/KSeCN

Autor: Jialiang Wu, Haofeng Shi, Xuemin Li, Jiaxin He, Chen Zhang, Fengxia Sun, Yunfei Du
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 20, Iss 1, Pp 1453-1461 (2024)
Druh dokumentu: article
ISSN: 1860-5397
83904638
DOI: 10.3762/bjoc.20.128
Popis: A series of 4-thio/seleno-cyanated pyrazoles was conveniently synthesized from 4-unsubstituted pyrazoles using NH4SCN/KSeCN as thio/selenocyanogen sources and PhICl2 as the hypervalent iodine oxidant. This metal-free approach was postulated to involve the in situ generation of reactive thio/selenocyanogen chloride (Cl–SCN/SeCN) from the reaction of PhICl2 and NH4SCN/KSeCN, followed by an electrophilic thio/selenocyanation of the pyrazole skeleton.
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