Multiple Approaches to the In Situ Generation of Anhydrous Tetraalkylammonium Fluoride Salts for SNAr Fluorination Reactions

MA Cismesia, SJ Ryan, DC Bland… - The Journal of Organic …, 2017 - ACS Publications
This article focuses on the development of practical approaches to the in situ generation of
anhydrous fluoride salts for applications in nucleophilic aromatic substitution (SNAr) …

Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination

MT Morales-Colón, YY See, SJ Lee, PJH Scott… - Organic …, 2021 - ACS Publications
Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the
formation of C (sp2)–F bonds. Despite many recent advances, a long-standing limitation of …

Anhydrous Tetramethylammonium Fluoride for Room-Temperature SNAr Fluorination

SD Schimler, SJ Ryan, DC Bland… - The Journal of …, 2015 - ACS Publications
This paper describes the room-temperature SNAr fluorination of aryl halides and nitroarenes
using anhydrous tetramethylammonium fluoride (NMe4F). This reagent effectively converts …

Development of SNAr Nucleophilic Fluorination: A Fruitful Academia-Industry Collaboration

YY See, MT Morales-Colón, DC Bland… - Accounts of Chemical …, 2020 - ACS Publications
Conspectus The identification of reliable, general, and high yielding methods for the
formation of C (sp2)–fluorine bonds remains a major challenge for synthetic organic …

Reactions of Arylsulfonate Electrophiles with NMe4F: Mechanistic Insight, Reactivity, and Scope

SD Schimler, RDJ Froese, DC Bland… - The Journal of Organic …, 2018 - ACS Publications
This paper describes a detailed study of the deoxyfluorination of aryl fluorosulfonates with
tetramethylammonium fluoride (NMe4F) and ultimately identifies other sulfonate …

Recycle waste salt as reagent: a one-pot substitution/Krapcho reaction sequence to α-fluorinated esters and sulfones

F Zhu, PW Xu, F Zhou, CH Wang, J Zhou - Organic letters, 2015 - ACS Publications
A “one-pot” tandem substitution/Krapcho reaction is reported for the facile synthesis of α-
fluorinated esters and sulfones, which utilizes the byproduct salt formed in the substitution …

Acyl azolium fluorides for room temperature nucleophilic aromatic fluorination of chloro-and nitroarenes

SJ Ryan, SD Schimler, DC Bland, MS Sanford - Organic letters, 2015 - ACS Publications
The reaction of acid fluorides with N-heterocyclic carbenes (NHCs) produces anhydrous
acyl azolium fluorides. With appropriate selection of acid fluoride and NHC, these salts can …

SNAr Reactions of Nitro-(pentafluorosulfanyl)benzenes To Generate SF5 Aryl Ethers and Sulfides

P Beier, T Pastyrikova, N Vida, G Iakobson - Organic letters, 2011 - ACS Publications
SNAr Reactions of Nitro-(pentafluorosulfanyl)benzenes To Generate SF5 Aryl Ethers and
Sulfides | Organic Letters ACS ACS Publications C&EN CAS Find my institution Log In Organic …

Traceless N‐Polyfluoroalkylation of Weakly Nucleophilic Nitrogen Containing Compounds

L Santos, F Audet, M Donnard… - … A European Journal, 2023 - Wiley Online Library
Here we report an efficient access to high‐value N‐polyfluoroalkyl anilines, primary
polyfluoroalkylamines and N, N‐bis (polyfluoroalkyl) amines, via N‐polyfluoroalkylation of …

One-pot fluorosulfurylation of Grignard reagents using sulfuryl fluoride

C Lee, ND Ball, GM Sammis - Chemical Communications, 2019 - pubs.rsc.org
Herein, we report a new method for the one-pot syntheses of sulfonyl fluorides. Addition of
an alkyl, aryl, or heteroaryl Grignard to a solution of sulfuryl fluoride at ambient temperature …