Deoxyfluorination of 1°, 2°, and 3° Alcohols by Nonbasic O–H Activation and Lewis Acid-Catalyzed Fluoride Shuttling,Journal of the American Chemical Society

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Deoxyfluorination of 1°, 2°, and 3° Alcohols by Nonbasic O–H Activation and Lewis Acid-Catalyzed Fluoride Shuttling
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2023-10-09 , DOI: 10.1021/jacs.3c08373
Hye Won Moon ₁ , Marissa N Lavagnino ₁ , Soohyun Lim ₁ , Maximilian D Palkowitz ₂ , Michael D Mandler ₃ , Gregory L Beutner ₄ , Myles J Drance ₁ , Jeffrey M Lipshultz ₁ , Paul M Scola ₂ , Alexander T Radosevich ₁

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A method for deoxyfluorination of aliphatic primary, secondary, and tertiary alcohols is reported, employing a nontrigonal phosphorus triamide for base-free alcohol activation in conjunction with an organic soluble fluoride donor and a triarylborane fluoride shuttling catalyst. Mechanistic experiments are consistent with a reaction that proceeds by the collapse of an oxyphosphonium fluoroborate ion pair with fluoride transfer. The substrate scope complements existing deoxyfluorination methods and enables the preparation of homochiral secondary and tertiary alkylfluorides by stereoinversion of the substrate alcohol.

中文翻译：

通过非碱性 O–H 活化和路易斯酸催化氟化物穿梭对 1°、2° 和 3° 醇进行脱氧氟化

报道了一种脂肪族伯醇、仲醇和叔醇脱氧氟化的方法，使用非三方磷三酰胺与有机可溶性氟化物供体和三芳基硼烷氟化物穿梭催化剂一起进行无碱醇活化。机理实验与氟硼酸氧鏻离子对塌陷和氟化物转移所进行的反应一致。该底物范围补充了现有的脱氧氟化方法，并能够通过底物醇的立体反转制备纯手性仲烷基氟和叔烷基氟。

更新日期：2023-10-09

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