Chinese Journal of Organic Chemistry >
Transition-Metal-Free Regioselective Thiocyanation of Triisopropylsilane (TIPS)-Protected Phenols
Received date: 2023-07-15
Revised date: 2023-09-12
Online published: 2023-11-23
Supported by
National Natural Science Foundation of China(22171197); Major Basic Research Project of the Natural Science Foundation of Jiangsu Higher Education Institutions(21KJA150002); National Local Joint Engineering Laboratory to Functional Adsorption Material Technology for Environmental Protection(SDGC2121); Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD); Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University
Arylthiocyanate compounds are crucial in organic chemistry. They have widespread applications in agrochemicals, pharmaceuticals, and materials chemistry. Herein, the transition metal-free regioselective thiocyanation of triisopropylsilane (TIPS)-protected phenol derivatives was achieved using NH4SCN as thiocyanation reagent and potassium peroxymonosulfonate/(2KHSO5•KHSO4•K2SO4, oxone) as the oxidant. The conversion was achieved in good to excellent yields under mild reaction conditions. Further, various functional groups were well tolerated in these reaction conditions. The practicability of this method was demonstrated in the thiocyanation of bioactive molecules, such as thymol, amylcresol, and phenethyl resorcinol.
Guodong Ju , Guangyu Zhou , Yingsheng Zhao . Transition-Metal-Free Regioselective Thiocyanation of Triisopropylsilane (TIPS)-Protected Phenols[J]. Chinese Journal of Organic Chemistry, 2024 , 44(4) : 1327 -1336 . DOI: 10.6023/cjoc202307015
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