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Et4NCl-Promoted Electrochemical Atherton-Todd Type Reaction to Construct P(O)–F Bonds
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-05-22 , DOI: 10.1021/acs.joc.3c00309
Hong Wang 1 , Xiangbin Li 1 , Yi Lu 1 , Lianxuan Wang 1 , Siyuan Liu 1 , Wei Gao 1 , Yonghe Tang 2 , Ling Wang 1 , Liwei Niu 1 , Jianbin Chen 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-05-22 , DOI: 10.1021/acs.joc.3c00309
Hong Wang 1 , Xiangbin Li 1 , Yi Lu 1 , Lianxuan Wang 1 , Siyuan Liu 1 , Wei Gao 1 , Yonghe Tang 2 , Ling Wang 1 , Liwei Niu 1 , Jianbin Chen 1
Affiliation
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An electrochemical synthetic strategy to construct P(O)–F bonds was developed via the Atherton–Todd reaction. Promoted by Et4NCl, a series of biologically active phosphoric fluorides were synthesized by use of commercially available P(O)–H feedstocks and Et3N·3HF as the F-source. With this protocol, some potentially functional P(O)–OR and P(O)–SR motifs could also be smoothly forged. This sustainable fluorination approach features step-economy, is chemical-oxidant- and metal-catalyst-free, and offers low cost and mild conditions. Additionally, cyclic voltammetry and control experiments were conducted to propose a reasonable mechanism.
中文翻译：
Et4NCl 促进电化学 Atherton-Todd 型反应构建 P(O)–F 键
通过 Atherton-Todd 反应开发了一种构建 P(O)-F 键的电化学合成策略。以市售P(O)–H为原料，以Et 3 N·3HF为氟源，在Et 4 NCl的催化下，合成了一系列具有生物活性的氟化磷。通过该协议，一些潜在功能性 P(O)–OR 和 P(O)–SR 基序也可以顺利伪造。这种可持续的氟化方法具有分步经济的特点，不含化学氧化剂和金属催化剂，并提供低成本和温和的条件。此外，还进行了循环伏安法和控制实验以提出合理的机理。
更新日期：2023-05-22
中文翻译：
Et4NCl 促进电化学 Atherton-Todd 型反应构建 P(O)–F 键
通过 Atherton-Todd 反应开发了一种构建 P(O)-F 键的电化学合成策略。以市售P(O)–H为原料，以Et 3 N·3HF为氟源，在Et 4 NCl的催化下，合成了一系列具有生物活性的氟化磷。通过该协议，一些潜在功能性 P(O)–OR 和 P(O)–SR 基序也可以顺利伪造。这种可持续的氟化方法具有分步经济的特点，不含化学氧化剂和金属催化剂，并提供低成本和温和的条件。此外，还进行了循环伏安法和控制实验以提出合理的机理。
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