Scalable Synthesis of the Shelf-Stable Radical Difluoromethylthiolation Reagent S-(Difluoromethyl)benzenesulfonothioate PhSO2SCF2H,Organic Process Research & Development

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Scalable Synthesis of the Shelf-Stable Radical Difluoromethylthiolation Reagent S-(Difluoromethyl)benzenesulfonothioate PhSO2SCF2H
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-05-24 , DOI: 10.1021/acs.oprd.3c00087
Xin Qiu ₁ , Wenrun Lou ₁ , Shengxue Zhang ₁ , Shengyajun Meng ₁ , Yong Guo ₂ , Xiaoyu Ma ₁ , Chao Liu _{1,

2} , Qilong Shen ₂

Affiliation

A procedure for the convenient preparation of an efficient radical difluoromethylthiolation reagent, namely, S-(difluoromethyl)benzenesulfonothioate (PhSO₂SCF₂H), was reported. The reagent was synthesized on an approximately 500 g scale in two steps from cheap commodity sodium benzene sulfinate, benzyl mercaptan, and HCF₂Cl. The key step of this protocol is to control the amount of chlorine and the reaction temperatures for the generation of key intermediate [HCF₂SCl]. Differential scanning calorimetry (DSC) was carried out to demonstrate the stability of PhSO₂SCF₂H. Furthermore, gram-scale reaction of PhSO₂SCF₂H with electron-rich aromatic (hetero)hydrocarbons, alkyl carboxylic acids, and olefins was demonstrated.

中文翻译：

货架稳定的自由基二氟甲基硫醇化试剂 S-(二氟甲基)苯硫代磺酸 PhSO2SCF2H 的可扩展合成

报道了一种方便制备有效的自由基二氟甲硫基化试剂即S- (二氟甲基)苯硫代磺酸盐 (PhSO ₂ SCF _{2 H) 的方法。}_{该试剂是从廉价商品苯亚磺酸钠、苄基硫醇和 HCF 2} Cl分两步以大约 500 g 的规模合成的。该协议的关键步骤是控制生成关键中间体 [HCF ₂ SCl] 的氯气量和反应温度。差示扫描量热法 (DSC) 用于证明 PhSO ₂ SCF _{2 H 的稳定性。此外，PhSO}₂ SCF ₂的克级反应证明了 H 与富电子芳烃（杂）烃、烷基羧酸和烯烃。

更新日期：2023-05-24

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