Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1327-1336.DOI: 10.6023/cjoc202307015 Previous Articles     Next Articles

ARTICLES

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

鞠国栋a, 周冠宇a, 赵应声a,b,*()   

  1. a 苏州大学材料与化学化工学部 江苏苏州 215123
    b 河南师范大学化学化工学院 河南新乡 453000
  • 收稿日期:2023-07-15 修回日期:2023-09-12 发布日期:2023-11-23
  • 基金资助:
    国家自然科学基金(22171197); 江苏省高等学校自然科学基金重大基础研究项目(21KJA150002); 环保功能吸附材料制备技术国地联合工程实验室开放课题(SDGC2121); 江苏高校优势学科建设工程; 河南师范大学化学化工学院开放基金资助项目.

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

Guodong Jua, Guangyu Zhoua, Yingsheng Zhaoa,b()   

  1. a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123
    b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453000
  • Received:2023-07-15 Revised:2023-09-12 Published:2023-11-23
  • Contact: E-mail: yszhao@suda.edu.cn
  • 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.

Key words: thiocyanation, triisopropylsilane (TIPS)-protected phenols, transition-metal-free, radical cation