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Quantification of the Activation Capabilities of Lewis/Brønsted Acid for Electrophilic Trifluoromethylthiolating Reagents†
Chinese Journal of Chemistry ( IF 5.4 ) Pub Date : 2019-12-24 , DOI: 10.1002/cjoc.201900412
Huiying Kang 1 , Biying Zhou 1 , Man Li 1 , Xiao‐Song Xue 1 , Jin‐Pei Cheng 1, 2
Affiliation  

Electrophilic trifluoromethylthiolation has emerged as an important and efficient methodology for installing the SCF3 moiety onto an array of organic molecules. Due to the low reactivities of trifluoromethylthiolating reagents, these transformations often require activation through an exogenous Lewis/Brønsted acid. We report herein the quantification of the activation capabilities of Lewis/Brønsted acids for trifluoromethylthiolating reagents through computing the difference in trifluoromethylthio cation donor ability (Tt+DA) between the "activated” and “unactivated” reagent. A moderate correlation is found to exist between the activation capability and Lewis acidity.

中文翻译:

路易斯/布朗斯台德酸对亲电子三氟甲基硫醇化试剂的活化能力的定量分析†

亲电子三氟甲基硫醇化已成为一种重要且有效的方法,用于将SCF 3部分安装到有机分子阵列上。由于三氟甲基硫醇化试剂的反应性低,这些转化通常需要通过外源的路易斯/布朗斯台德酸进行活化。我们通过计算“活化”和“未活化”试剂之间三氟甲硫基阳离子供体能力(Tt + DA)的差异,报告了路易斯/布朗斯台德酸对三氟甲硫基化试剂的活化能力的定量。活化能力和路易斯酸度。
更新日期:2019-12-25
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