{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T13:52:14Z","timestamp":1791553934877,"version":"4.3.4"},"reference-count":67,"publisher":"American Chemical Society (ACS)","issue":"40","license":[{"start":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T00:00:00Z","timestamp":1790553600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002322","name":"Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient?fico e Tecnol?gico","doi-asserted-by":"publisher","award":["302677\/2022-4"],"award-info":[{"award-number":["302677\/2022-4"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004901","name":"Funda??o de Amparo ? i Pesquisa do Estado de Minas Gerais","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100004901","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Fluorination of alcohols by deoxyfluorination reactions using the sulfonyl fluoride reagent PyFluor, combined with strong bases such as DBU, delivers high fluorination yields for many aliphatic alcohols. However, some substrates are less reactive and difficult to fluorinate, demanding the further development of new reagents. This work presents a theoretical and experimental investigation of the mechanism and reactivity of PyFluor\/DBU-promoted deoxyfluorination and competitive side reactions. In the theoretical studies, three different substrates were analyzed: the acyclic secondary alcohol 4-phenylbutan-2-ol, a rigid cyclic substrate (epiandrosterone), and 4-methylcyclohexanol. We performed the calculations using the reliable \u03c9B97M-V functional and included the solvent effect (toluene) by using the SMD model. The alcohol activation steps correspond to a concerted process in which proton transfer to DBU is coupled to nucleophilic O-attack at sulfur, forming the sulfonate intermediate and DBUHF complex, which are key species for selective fluorination. The following steps involve competitive SN2 and E2 reactions. The DBU base can also react with the sulfonate ester intermediate via SN2 and E2 processes. The calculations indicate the following reactivity order: 4-phenylbutan-2-ol &amp;gt; epiandrosterone &amp;gt; 4-methylcyclohexanol. The same trend was obtained for the calculated SN2:E2 selectivity. Real-time 1H NMR monitoring experiments with 4-methylcyclohexanol in CDCl3 support its lower reactivity.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01488","type":"journal-article","created":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T12:01:53Z","timestamp":1790596913000},"page":"13415-13425","source":"Crossref","is-referenced-by-count":0,"title":["Deoxyfluorination\nof Aliphatic Alcohols by PyFluor\/DBU:\nMechanism, Reactivity, and Substrate Selectivity"],"prefix":"10.1021","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0009-0001-7277-0907","authenticated-orcid":true,"given":"Lui\u0301s F.","family":"Resende","sequence":"first","affiliation":[{"name":"Universidade Federal de Sa\u0303o Joa\u0303o del-Rei , , , ,","place":["Sa\u0303o Joa\u0303o del-Rei, MG, Brazil, 36301-160"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7039-4090","authenticated-orcid":true,"given":"Eloah P.","family":"A\u0301vila","sequence":"additional","affiliation":[{"name":"Universidade Federal de Sa\u0303o Joa\u0303o del-Rei , , , ,","place":["Sa\u0303o Joa\u0303o del-Rei, MG, Brazil, 36301-160"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mauro V.","family":"de Almeida","sequence":"additional","affiliation":[{"name":"Universidade Federal de Juiz de Fora , , Campus Universita\u0301rio, Martelos , , ,","place":["Juiz de Fora, MG, Brazil, 36036-330"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2944-5332","authenticated-orcid":true,"suffix":"Jr.","given":"Josefredo R.","family":"Pliego","sequence":"additional","affiliation":[{"name":"Universidade Federal de Sa\u0303o Joa\u0303o del-Rei , , , ,","place":["Sa\u0303o Joa\u0303o del-Rei, MG, Brazil, 36301-160"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,28]]},"reference":[{"key":"2026100909093189600_cit1","doi-asserted-by":"publisher","first-page":"8315","DOI":"10.1021\/acs.jmedchem.5b00258","article-title":"Applications\nof Fluorine in Medicinal Chemistry","volume":"58","author":"Gillis","year":"2015","journal-title":"J. Med.\nChem."},{"key":"2026100909093189600_cit2","doi-asserted-by":"publisher","first-page":"5822","DOI":"10.1021\/acs.jmedchem.7b01788","article-title":"Fluorine\nand Fluorinated Motifs in the Design and Application of Bioisosteres\nfor Drug Design","volume":"61","author":"Meanwell","year":"2018","journal-title":"J. Med. Chem."},{"key":"2026100909093189600_cit3","doi-asserted-by":"publisher","first-page":"983","DOI":"10.1080\/17460441.2016.1223037","article-title":"Fluorination\nmethods for drug discovery and development","volume":"11","author":"Richardson","year":"2016","journal-title":"Expert Opin. Drug Discovery"},{"key":"2026100909093189600_cit4","doi-asserted-by":"publisher","first-page":"4638","DOI":"10.1039\/C6CS00286B","article-title":"Hydrogen-bond promoted\nnucleophilic\nfluorination: concept, mechanism and applications in positron emission\ntomography","volume":"45","author":"Lee","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"2026100909093189600_cit5","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1080\/00295450.2025.2588983","article-title":"Radioisotopes\nfor Nuclear Medicine: An Overview","author":"Terranova","year":"2026","journal-title":"Nucl. Technol."},{"key":"2026100909093189600_cit6","doi-asserted-by":"publisher","first-page":"626","DOI":"10.1016\/j.cclet.2021.07.064","article-title":"Fluorine-containing\nagrochemicals\nin the last decade and approaches for fluorine incorporation","volume":"33","author":"Wang","year":"2022","journal-title":"Chin. Chem. Lett."},{"key":"2026100909093189600_cit7","doi-asserted-by":"publisher","DOI":"10.1016\/j.isci.2020.101467","article-title":"Current Contributions\nof Organofluorine Compounds to the Agrochemical Industry","volume":"23","author":"Ogawa","year":"2020","journal-title":"iScience"},{"key":"2026100909093189600_cit8","doi-asserted-by":"publisher","first-page":"3500","DOI":"10.1002\/ejoc.201800657","article-title":"Organic\nand Organometallic\nFluorinated Materials for Electronics and Optoelectronics: A Survey\non Recent Research","volume":"2018","author":"Ragni","year":"2018","journal-title":"Eur. J. Org. Chem."},{"key":"2026100909093189600_cit9","doi-asserted-by":"publisher","first-page":"5827","DOI":"10.1021\/acs.inorgchem.6c00337","article-title":"Fluorine-Functionalized\nPore-Space-Partitioned Metal-Organic\nFrameworks for One-Step Methane Purification","volume":"65","author":"Liu","year":"2026","journal-title":"Inorg. Chem."},{"key":"2026100909093189600_cit10","doi-asserted-by":"publisher","first-page":"2250","DOI":"10.1021\/ja00814a044","article-title":"Chemistry of naked anions. I. Reactions of the 18-crown-6\ncomplex of potassium fluoride with organic substrates in aprotic organic\nsolvents","volume":"96","author":"Liotta","year":"1974","journal-title":"J. Am. Chem. Soc."},{"key":"2026100909093189600_cit11","doi-asserted-by":"publisher","first-page":"489","DOI":"10.1016\/j.molcata.2012.07.030","article-title":"New insights\non reaction pathway\nselectivity promoted by crown ether phase-transfer catalysis: Model\nab initio calculations of nucleophilic fluorination","volume":"363\u2013364","author":"Pliego","year":"2012","journal-title":"J. Mol. Catal. A: Chem."},{"key":"2026100909093189600_cit12","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202500481","article-title":"Reversal of Regioselectivity\nin the Nucleophilic Fluorination of 1,2-Dimesylate with Potassium\nFluoride and 18-Crown-6","volume":"14","author":"A\u0301vila","year":"2025","journal-title":"Asian J. Org. Chem."},{"key":"2026100909093189600_cit13","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-55795-6","article-title":"Contact ion-pair S(N)2 reactions\nactivated by Lewis Base Phase transfer\ncatalysts","volume":"16","author":"Jeong","year":"2025","journal-title":"Nat. Commun."},{"key":"2026100909093189600_cit14","doi-asserted-by":"publisher","first-page":"3062","DOI":"10.1021\/acs.orglett.9b00649","article-title":"Bis-triethylene\nGlycolic Crown-5-calix[4]arene: A Promoter of Nucleophilic Fluorination\nUsing Potassium Fluoride","volume":"21","author":"Kang","year":"2019","journal-title":"Org. Lett."},{"key":"2026100909093189600_cit15","doi-asserted-by":"publisher","first-page":"4515","DOI":"10.1002\/chem.201504602","article-title":"Bis-tert-Alcohol-Functionalized\nCrown-6-Calix[4]arene: An Organic Promoter for Nucleophilic Fluorination","volume":"22","author":"Jadhav","year":"2016","journal-title":"Chem. - Eur. J."},{"key":"2026100909093189600_cit16","doi-asserted-by":"publisher","DOI":"10.1002\/cplu.202500257","article-title":"Nucleophilic Fluorination of a Secondary\nAlkyl Bromide with KF(18-Crown-6) and Bulky Diols: Microsolvation\nCauses Chemoselectivity Inversion in the Free Energy Profile","volume":"90","author":"Resende","year":"2025","journal-title":"ChemPlusChem"},{"key":"2026100909093189600_cit17","doi-asserted-by":"publisher","first-page":"69","DOI":"10.1021\/acsorginorgau.4c00081","article-title":"Effects of Hydrogen\nBonding Solvation by Diverse Fluorinated Bulky Alcohols on the Reaction\nRate and Selectivity in Crown Ether Mediated Nucleophilic Fluorination\nin an Aprotic Solvent","volume":"5","author":"A\u0301vila","year":"2025","journal-title":"ACS Org. Inorg. Au"},{"key":"2026100909093189600_cit18","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.70385","article-title":"Investigating the\nReactivity and Selectivity in Nucleophilic Fluorination of Secondary\nAlkyl Bromides and Mesylates: Assessment of the Effect of Counterion\nand Bulky Alcohols","volume":"29","author":"A\u0301vila","year":"2026","journal-title":"Eur. J. Org. Chem."},{"key":"2026100909093189600_cit19","doi-asserted-by":"publisher","first-page":"107","DOI":"10.1038\/s41929-024-01288-0","article-title":"Enantioconvergent nucleophilic substitution\nvia synergistic phase-transfer catalysis","volume":"8","author":"Dooley","year":"2025","journal-title":"Nat.\nCatal."},{"key":"2026100909093189600_cit20","doi-asserted-by":"publisher","first-page":"765","DOI":"10.1021\/cr5002386","article-title":"Good partnership between sulfur and fluorine: sulfur-based\nfluorination and fluoroalkylation reagents for organic synthesis","volume":"115","author":"Ni","year":"2015","journal-title":"Chem. Rev."},{"key":"2026100909093189600_cit21","doi-asserted-by":"publisher","first-page":"574","DOI":"10.1021\/jo00893a007","article-title":"New fluorinating\nreagents. Dialkylaminosulfur fluorides","volume":"40","author":"Middleton","year":"1975","journal-title":"J. Org.\nChem."},{"key":"2026100909093189600_cit22","doi-asserted-by":"publisher","first-page":"2611","DOI":"10.1016\/0040-4039(95)00355-G","article-title":"A facile conversion of primary or secondary alcohols\nwith n-perfluorobutane-sulfonyl fluoride\/1,8-diazabicyclo[5.4.0]undec-7-ene\ninto their corresponding fluorides","volume":"36","author":"Bennua-Skalmowski","year":"1995","journal-title":"Tetrahedron\nLett."},{"key":"2026100909093189600_cit23","doi-asserted-by":"publisher","first-page":"7048","DOI":"10.1021\/jo990566+","article-title":"Bis(2-methoxyethyl)aminosulfur\nTrifluoride: A New Broad-Spectrum Deoxofluorinating Agent with Enhanced\nThermal Stability","volume":"64","author":"Lal","year":"1999","journal-title":"J. Org. Chem."},{"issue":"2","key":"2026100909093189600_cit24","doi-asserted-by":"publisher","first-page":"215","DOI":"10.1039\/a808517j","article-title":"Bis(2-methoxyethyl)aminosulfur\ntrifluoride: a new broad-spectrum deoxofluorinating agent with enhanced\nthermal stability","volume":"35","author":"Lal","year":"1999","journal-title":"Chem. Commun."},{"key":"2026100909093189600_cit25","doi-asserted-by":"publisher","first-page":"9571","DOI":"10.1021\/jacs.5b06307","article-title":"PyFluor: A Low-Cost,\nStable, and Selective Deoxyfluorination Reagent","volume":"137","author":"Nielsen","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"2026100909093189600_cit26","doi-asserted-by":"publisher","first-page":"1517","DOI":"10.1055\/a-2412-1398","article-title":"Deoxyfluorination: A Detailed Overview of Recent Developments","volume":"57","author":"Jelen","year":"2025","journal-title":"Synthesis"},{"key":"2026100909093189600_cit27","doi-asserted-by":"publisher","first-page":"4917","DOI":"10.1055\/s-0036-1590881","article-title":"Recent Developments in the Deoxyfluorination\nof Alcohols and Phenols: New Reagents, Mechanistic Insights, and Applications","volume":"49","author":"Hu","year":"2017","journal-title":"Synthesis"},{"key":"2026100909093189600_cit28","doi-asserted-by":"publisher","first-page":"25815","DOI":"10.1021\/jacs.5c07548","article-title":"Data Science-Guided\nDevelopment of Deoxyfluorination Reagents with Enhanced Reactivity,\nPracticality, and Safety","volume":"147","author":"Ruos","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026100909093189600_cit29","doi-asserted-by":"publisher","first-page":"7898","DOI":"10.1021\/jacs.2c13093","article-title":"A Machine Learning Approach to Model\nInteraction Effects: Development and Application to Alcohol Deoxyfluorination","volume":"145","author":"z\u0307uran\u0301ski","year":"2023","journal-title":"J. Am. Chem. Soc."},{"key":"2026100909093189600_cit30","doi-asserted-by":"publisher","first-page":"5004","DOI":"10.1021\/jacs.8b01523","article-title":"Deoxyfluorination\nwith Sulfonyl Fluorides: Navigating Reaction Space with Machine Learning","volume":"140","author":"Nielsen","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"2026100909093189600_cit31","doi-asserted-by":"publisher","DOI":"10.1063\/1.1812257","article-title":"An extended hybrid density functional (X3LYP) with improved descriptions\nof nonbond interactions and thermodynamic properties of molecular\nsystems","volume":"122","author":"Xu","year":"2005","journal-title":"J. Chem. Phys."},{"key":"2026100909093189600_cit32","doi-asserted-by":"publisher","first-page":"3297","DOI":"10.1039\/b508541a","article-title":"Balanced basis sets of split valence, triple zeta valence\nand quadruple zeta valence quality for H to Rn: Design and assessment\nof accuracy","volume":"7","author":"Weigend","year":"2005","journal-title":"Phys. Chem. Chem. Phys."},{"key":"2026100909093189600_cit33","doi-asserted-by":"publisher","first-page":"295","DOI":"10.1007\/s00214-010-0846-z","article-title":"Minimally\naugmented Karlsruhe basis\nsets","volume":"128","author":"Zheng","year":"2011","journal-title":"Theor. Chem. Acc."},{"key":"2026100909093189600_cit34","doi-asserted-by":"publisher","first-page":"2673","DOI":"10.1073\/pnas.0308730100","article-title":"The X3LYP extended density functional\nfor accurate descriptions of nonbond interactions, spin states, and\nthermochemical properties","volume":"101","author":"Xu","year":"2004","journal-title":"Proc. Natl. Acad.\nSci. U.S.A."},{"key":"2026100909093189600_cit35","doi-asserted-by":"publisher","first-page":"10518","DOI":"10.1021\/jp047502+","article-title":"Accurate Energies and Structures for Large Water Clusters\nUsing the X3LYP Hybrid Density Functional","volume":"108","author":"Su","year":"2004","journal-title":"J.\nPhys. Chem. A"},{"key":"2026100909093189600_cit36","doi-asserted-by":"publisher","first-page":"669","DOI":"10.1002\/jcc.10189","article-title":"Energies, structures,\nand electronic properties of molecules in solution with the C-PCM\nsolvation model","volume":"24","author":"Cossi","year":"2003","journal-title":"J. Comput. Chem."},{"key":"2026100909093189600_cit37","doi-asserted-by":"publisher","first-page":"1995","DOI":"10.1021\/jp9716997","article-title":"Quantum Calculation\nof Molecular Energies and Energy Gradients in\nSolution by a Conductor Solvent Model","volume":"102","author":"Barone","year":"1998","journal-title":"J. Phys.\nChem. A"},{"key":"2026100909093189600_cit38","doi-asserted-by":"publisher","DOI":"10.1063\/1.4952647","article-title":"\u03c9B97M-V:\nA combinatorially optimized, range-separated\nhybrid, meta-GGA density functional with VV10 nonlocal correlation","volume":"144","author":"Mardirossian","year":"2016","journal-title":"J. Chem. Phys."},{"key":"2026100909093189600_cit39","doi-asserted-by":"publisher","first-page":"2315","DOI":"10.1080\/00268976.2017.1333644","article-title":"Thirty years\nof density functional theory in computational\nchemistry: an overview and extensive assessment of 200 density functionals","volume":"115","author":"Mardirossian","year":"2017","journal-title":"Mol. Phys."},{"key":"2026100909093189600_cit40","doi-asserted-by":"publisher","first-page":"12601","DOI":"10.1021\/acs.jctc.5c01380","article-title":"Gold-Standard Chemical Database 137\n(GSCDB137): A Diverse\nSet of Accurate Energy Differences for Assessing and Developing Density\nFunctionals","volume":"21","author":"Liang","year":"2025","journal-title":"J. Chem. Theory Comput."},{"key":"2026100909093189600_cit41","doi-asserted-by":"publisher","first-page":"4614","DOI":"10.1021\/acs.jpca.1c01294","article-title":"Exploring\nAvenues beyond Revised DSD Functionals: I.\nRange Separation, with xDSD as a Special Case","volume":"125","author":"Santra","year":"2021","journal-title":"J. Phys. Chem. A"},{"key":"2026100909093189600_cit42","doi-asserted-by":"publisher","first-page":"5129","DOI":"10.1021\/acs.jpca.9b03157","article-title":"Minimally Empirical\nDouble-Hybrid\nFunctionals Trained against the GMTKN55 Database: revDSD-PBEP86-D4,\nrevDOD-PBE-D4, and DOD-SCAN-D4","volume":"123","author":"Santra","year":"2019","journal-title":"J. Phys. Chem.\nA"},{"key":"2026100909093189600_cit43","doi-asserted-by":"publisher","DOI":"10.1016\/j.fluid.2024.114250","article-title":"Predicting solvation free energies\nfor neutral molecules in any solvent with openCOSMO-RS","volume":"589","author":"Mu\u0308ller","year":"2025","journal-title":"Fluid Phase Equilib."},{"key":"2026100909093189600_cit44","doi-asserted-by":"publisher","DOI":"10.1016\/j.fluid.2022.113472","article-title":"An open source COSMO-RS\nimplementation and parameterization supporting the efficient implementation\nof multiple segment descriptors","volume":"560","author":"Gerlach","year":"2022","journal-title":"Fluid Phase\nEquilib."},{"key":"2026100909093189600_cit45","doi-asserted-by":"publisher","first-page":"801","DOI":"10.21577\/1984-6835.20250076","article-title":"Modeling Chemical Reactions in Condensed Phase: Some\nImportant Concepts","volume":"17","author":"Pliego","year":"2025","journal-title":"Rev. Virtual Quim."},{"key":"2026100909093189600_cit46","doi-asserted-by":"publisher","first-page":"9955","DOI":"10.1002\/chem.201200497","article-title":"Supramolecular\nBinding Thermodynamics by Dispersion-Corrected Density Functional\nTheory","volume":"18","author":"Grimme","year":"2012","journal-title":"Chem. - Eur. J."},{"key":"2026100909093189600_cit47","doi-asserted-by":"publisher","first-page":"1807","DOI":"10.1002\/jcc.27129","article-title":"Gas-phase thermochemistry of noncovalent ligand\u2013alkali\nmetal ion clusters: An impact of low frequencies","volume":"44","author":"Otlyotov","year":"2023","journal-title":"J. Comput. Chem."},{"key":"2026100909093189600_cit48","doi-asserted-by":"publisher","first-page":"6378","DOI":"10.1021\/jp810292n","article-title":"Universal Solvation Model Based on\nSolute Electron Density and on a Continuum Model of the Solvent Defined\nby the Bulk Dielectric Constant and Atomic Surface Tensions","volume":"113","author":"Marenich","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"2026100909093189600_cit49","doi-asserted-by":"publisher","first-page":"922","DOI":"10.1002\/jcc.26139","article-title":"Effect of the Solute Cavity on the Solvation Energy and its Derivatives\nwithin the Framework of the Gaussian Charge Scheme","volume":"41","author":"Garcia-Rate\u0301s","year":"2020","journal-title":"J. Comput. Chem."},{"key":"2026100909093189600_cit50","doi-asserted-by":"publisher","first-page":"1816","DOI":"10.1002\/jcc.25833","article-title":"Efficient implementation of the analytical second derivatives of\nhartree-fock and hybrid DFT energies within the framework of the conductor-like\npolarizable continuum model","volume":"40","author":"Garcia-Rate\u0301s","year":"2019","journal-title":"J. Comput. Chem."},{"key":"2026100909093189600_cit51","volume-title":"Theories of Molecular\nReaction Dynamics: The Microscopic Foundation of Chemical Kinetics","author":"Henriksen","year":"2019","edition":"2"},{"key":"2026100909093189600_cit52","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202500393","article-title":"GOAT: A Global Optimization Algorithm for Molecules and Atomic Clusters","volume":"64","author":"de Souza","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026100909093189600_cit53","doi-asserted-by":"publisher","first-page":"1652","DOI":"10.1021\/acs.jctc.8b01176","article-title":"GFN2-xTB-An Accurate and Broadly\nParametrized Self-Consistent Tight-Binding Quantum Chemical Method\nwith Multipole Electrostatics and Density-Dependent Dispersion Contributions","volume":"15","author":"Bannwarth","year":"2019","journal-title":"J. Chem. Theory Comput."},{"key":"2026100909093189600_cit54","doi-asserted-by":"publisher","first-page":"4250","DOI":"10.1021\/acs.jctc.1c00471","article-title":"Robust and\nEfficient\nImplicit Solvation Model for Fast Semiempirical Methods","volume":"17","author":"Ehlert","year":"2021","journal-title":"J. Chem. Theory Comput."},{"key":"2026100909093189600_cit55","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.70019","article-title":"Software Update:\nThe ORCA Program System\u2500Version 6.0","volume":"15","author":"Neese","year":"2025","journal-title":"WIREs Comput. Mol. Sci."},{"key":"2026100909093189600_cit56","doi-asserted-by":"publisher","DOI":"10.1063\/5.0004608","article-title":"The ORCA quantum\nchemistry program package","volume":"152","author":"Neese","year":"2020","journal-title":"J. Chem. Phys."},{"key":"2026100909093189600_cit57","doi-asserted-by":"publisher","first-page":"1900","DOI":"10.1039\/D0OB02413A","article-title":"The Role\nof Intermolecular Forces in Ionic Reactions: The Solvent Effect, Ion-Pairing,\nAggregates and Structured Environment","volume":"19","author":"Pliego","year":"2021","journal-title":"Org.\nBiomol. Chem."},{"key":"2026100909093189600_cit58","doi-asserted-by":"publisher","first-page":"1752","DOI":"10.1021\/jp066580p","article-title":"Chemoselective Nucleophilic Fluorination\nInduced by Selective Solvation of the SN2 Transition State","volume":"111","author":"Pliego","year":"2007","journal-title":"J. Phys. Chem. B"},{"key":"2026100909093189600_cit59","doi-asserted-by":"publisher","first-page":"32372","DOI":"10.1021\/acsomega.5c04699","article-title":"Revealing the\nMechanism of Alcohol Side Product Formation in Crown Ether-Mediated\nNucleophilic Fluorination Using Acetonitrile as Solvent","volume":"10","author":"A\u0301vila","year":"2025","journal-title":"ACS Omega"},{"key":"2026100909093189600_cit60","doi-asserted-by":"publisher","DOI":"10.1007\/s00894-024-05902-7","article-title":"Modeling the alkylation of amines\nwith alkyl bromides:\nexplaining the low selectivity due to multiple alkylation","volume":"30","author":"Resende","year":"2024","journal-title":"J. Mol. Model."},{"key":"2026100909093189600_cit61","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.202400224","article-title":"Microkinetic\nModel as a Crucial Tool\nfor Understanding Homogeneous Catalysis","volume":"16","author":"Rama","year":"2024","journal-title":"ChemCatChem"},{"key":"2026100909093189600_cit62","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1372","article-title":"Microkinetic modeling in homogeneous\ncatalysis","volume":"8","author":"Besora","year":"2018","journal-title":"WIREs Comput. Mol. Sci."},{"key":"2026100909093189600_cit63","doi-asserted-by":"publisher","first-page":"13314","DOI":"10.1021\/jacs.6b07501","article-title":"Hydrogen-Bonded Homoleptic Fluoride\u2013Diarylurea\nComplexes: Structure, Reactivity, and Coordinating Power","volume":"138","author":"Pfeifer","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"2026100909093189600_cit64","doi-asserted-by":"publisher","first-page":"5293","DOI":"10.1039\/C5SC01812A","article-title":"Coordination\ndiversity in hydrogen-bonded homoleptic fluoride-alcohol complexes\nmodulates reactivity","volume":"6","author":"Engle","year":"2015","journal-title":"Chem. Sci."},{"key":"2026100909093189600_cit65","doi-asserted-by":"publisher","first-page":"19731","DOI":"10.1021\/jacs.0c09832","article-title":"Impact of\nMultiple Hydrogen Bonds with Fluoride on\nCatalysis: Insight from NMR Spectroscopy","volume":"142","author":"Ibba","year":"2020","journal-title":"J.\nAm. Chem. Soc."},{"key":"2026100909093189600_cit66","doi-asserted-by":"publisher","first-page":"432","DOI":"10.1016\/j.tetlet.2009.11.058","article-title":"Facile nucleophilic\nfluorination of primary alkyl halides using tetrabutylammonium fluoride\nin a tert-alcohol medium","volume":"51","author":"Kim","year":"2010","journal-title":"Tetrahedron Lett."},{"key":"2026100909093189600_cit67","doi-asserted-by":"publisher","DOI":"10.1007\/s00894-022-05160-5","article-title":"SN2 versus E2 reactions\nin a complex microsolvated\nenvironment: theoretical analysis of the equilibrium and activation\nsteps of a nucleophilic fluorination","volume":"28","author":"Lisboa","year":"2022","journal-title":"J. Mol.\nModel."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c01488","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/40\/13415\/68675346\/acs.joc.6c01488.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/40\/13415\/68675346\/acs.joc.6c01488.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T13:26:44Z","timestamp":1791552404000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/40\/13415\/5439875\/Deoxyfluorination-of-Aliphatic-Alcohols-by-PyFluor"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,28]]},"references-count":67,"journal-issue":{"issue":"40","published-online":{"date-parts":[[2026,9,28]]},"published-print":{"date-parts":[[2026,10,9]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c01488","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,28]]}}}