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Rapid Deoxyfluorination of Alcohols with N‐Tosyl‐4‐chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor) at Room Temperature
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2019-04-26 , DOI: 10.1002/chem.201901176
Junkai Guo 1 , Cuiwen Kuang 1 , Jian Rong 1 , Lingchun Li 1 , Chuanfa Ni 1 , Jinbo Hu 1
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2019-04-26 , DOI: 10.1002/chem.201901176
Junkai Guo 1 , Cuiwen Kuang 1 , Jian Rong 1 , Lingchun Li 1 , Chuanfa Ni 1 , Jinbo Hu 1
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The deoxyfluorination of alcohols is a fundamentally important approach to access alkyl fluorides, and thus the development of shelf‐stable, easy‐to‐handle, fluorine‐economical, and highly selective deoxyfluorination reagents is highly desired. This work describes the development of a crystalline compound, N‐tosyl‐4‐chlorobenzenesulfonimidoyl fluoride (SulfoxFluor), as a novel deoxyfluorination reagent that possesses all of the aforementioned merits, which is rare in the arena of deoxyfluorination. Endowed by the multi‐dimensional modulating ability of the sulfonimidoyl group, SulfoxFluor is superior to 2‐pyridinesulfonyl fluoride (PyFluor) in fluorination rate, and is also superior to perfluorobutanesulfonyl fluoride (PBSF) in fluorine‐economy. Its reaction with alcohols not only tolerates a wide range of functionalities including the more sterically hindered alcoholic hydroxyl groups, but also exhibits high fluorination/elimination selectivity. Because SulfoxFluor can be easily prepared from inexpensive materials and can be safely handled without special techniques, it promises to serve as a practical deoxyfluorination reagent for the synthesis of various alkyl fluorides.
中文翻译：
在室温下使用N-甲苯磺酰基-4-氯苯磺酰亚氨基氟化物（SulfoxFluor）对醇进行快速脱氧氟化
醇类的脱氧氟化是获取烷基氟化物的最基本的方法，因此，迫切需要开发出耐贮存，易处理，氟经济且高选择性的脱氧氟化试剂。这项工作描述了结晶化合物N的发展甲苯磺酰基-4-氯苯磺酰亚胺基氟（SulfoxFluor），作为一种新型的脱氧氟化剂，具有上述所有优点，在脱氧氟化领域是罕见的。由于具有磺酰亚胺基的多维调节能力，SulfoxFluor的氟化速率优于2-吡啶磺酰氟（PyFluor），并且在氟经济方面也优于全氟丁烷磺酰氟（PBSF）。它与醇的反应不仅可以耐受各种功能，包括受空间位阻更大的醇羟基，而且还具有很高的氟化/消除选择性。由于SulfoxFluor可以轻松地由廉价的材料制成，并且无需特殊技术即可安全地进行处理，
更新日期：2019-04-26
中文翻译：
在室温下使用N-甲苯磺酰基-4-氯苯磺酰亚氨基氟化物（SulfoxFluor）对醇进行快速脱氧氟化
醇类的脱氧氟化是获取烷基氟化物的最基本的方法，因此，迫切需要开发出耐贮存，易处理，氟经济且高选择性的脱氧氟化试剂。这项工作描述了结晶化合物N的发展甲苯磺酰基-4-氯苯磺酰亚胺基氟（SulfoxFluor），作为一种新型的脱氧氟化剂，具有上述所有优点，在脱氧氟化领域是罕见的。由于具有磺酰亚胺基的多维调节能力，SulfoxFluor的氟化速率优于2-吡啶磺酰氟（PyFluor），并且在氟经济方面也优于全氟丁烷磺酰氟（PBSF）。它与醇的反应不仅可以耐受各种功能，包括受空间位阻更大的醇羟基，而且还具有很高的氟化/消除选择性。由于SulfoxFluor可以轻松地由廉价的材料制成，并且无需特殊技术即可安全地进行处理，
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