Recent Developments in the Deoxyfluorination of Alcohols and Phenols: New Reagents, Mechanistic Insights, and Applications

Abstract

This short review describes the development of new reagents and methods for the deoxyfluorination of phenols and alcohols during the period of 2011 to 2017. Important advances in the mechanistic understanding of these processes are discussed. The continuing importance of deoxyfluorination chemistry for the synthesis of valuable target molecules is highlighted through case studies including examples of 18F-radiosynthesis and the preparation of exotic multifluorinated compounds.1 Introduction2 New Deoxyfluorination Reagents3 Novel Applications of ‘Legacy’ Deoxyfluorinating Reagents4 Conclusions and Future Directions

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates

“…Nucleophilic fluorination is one of the fundamental reactions in organic chemistry in the field of the synthesis of building blocks with a potential biological activity. To date, scientists have developed many nucleophilic fluorinating reagents [17][18][19]. Among others, we can distinguish a family of such chemicals having in their structure a sulfonyl fluoride system.…”

Light‐Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single‐Electron Oxidation with TEDA2+.

“…Nucleophilic deoxyfluorination reactions constitute one of the main strategies fort he construction of aliphatic CÀFb onds. [1] Historically,D AST (diethylaminosulfur trifluoride)h as been the primary deoxyfluorination reagent; [2] nevertheless,d ue to its intrinsic reactivity it suffers from limited functional-group tolerance. This has prompted the development of milder and more effective deoxyfluorination reagents, such as PyFluor by Doyle, [3] or PhenoFluor [4] and AlkylFluor by Ritter.…”

Recent trends in dehydroxylative trifluoro-methylation, -methoxylation, -methylthiolation, and -methylselenylation of alcohols

“…[6][7][8][9] In recent years, direct dehydroxylative functionalization of alcohols has become one of the hottest research topics in organic chemistry because it is a powerful and general strategy for the construction of various valuable functionalized organic compounds from inexpensive and abundantly available alcohols without isolation of intermediates. 10 In this regard, dehydroxylative triuoro-methylation, -methoxylation, -methylthiolation, and -methylselenylation of alcohols have captured the imagination of the organic chemical community and have become promising synthetic methods for constructing C-CF 3 , C-OCF 3 , C-SCF 3 , and C-SeCF 3 bonds, respectively. These synthetic processes are advantageous because the starting materials possess high selectivity and stability, are abundant and inexpensive, with low toxicity, and there is no need for isolation of intermediates.…”