三异丙基硅烷(TIPS)保护苯酚的无过渡金属催化区域选择性硫氰化反应

Transition-Metal-Free Regioselective Thiocyanation of Triisopropylsilane(TIPS)-Protected Phenols

芳基硫氰酸酯化合物在有机化学中非常重要,广泛存在于农用化学品、药品和材料中.以NH_(4)SCN为硫氰化试剂,过氧单磺酸钾/(2KHSO_(5)·KHSO_(4)·K_(2)SO_(4),oxone)为氧化剂,实现了三异丙基硅烷(TIPS)保护的苯酚衍生物无过渡金属催化区域选择性硫氰化反应.在温和的反应条件下,以良好至优异的收率实现了转化,并且多种官能团对反应条件都有良好的耐受性.该方法的实用性在麝香草酚、戊甲酚和苯乙基间苯二酚等生物活性分子的硫氰化反应中得到了很好的体现.

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 NH_(4)SCN as thiocyanation reagent and potassium peroxymonosulfonate/(2KHSO_(5)·KHSO_(4)·K_(2)SO_(4),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.