title: Formation of α-SF5-Enolate Enables Preparation of 3-SF5-Quinolin-2-ones, 3-SF5-Quinolines, and 3-SF5-Pyridin-2-ones: Evaluation of their Physicochemical Properties.
abstract: This study describes, for the first time, the generation of a SF5 -substituted ester enolate from benzyl SF5 -acetate under soft enolization conditions, which in turn participates in aldol addition reactions in high yield. The reaction was applied in the synthesis of 3-SF5 -quinolin-2-ones, 3-SF5 -quinolines, and 3-SF5 -pyridin-2-ones, none of which have previously been reported. To provide guidelines for their use in drug discovery, the physicochemical properties of these building blocks were determined and compared with those of their CF3 - and t-Bu-analogues.
authors.affiliation: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
authors.forename: Adrien
authors.initials: A
authors.lastname: Joliton
authors.affiliation: Pharmaceutical Research and Early Development, Roche Innovation Center Basel, F. Hoffmann-La Roche Ltd., Grenzacherstrasse 124, 4070, Basel, Switzerland.
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Plancher
authors.affiliation: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland. carreira@org.chem.ethz.ch.
authors.forename: Erick M
authors.identifier: http://orcid.org/0000-0003-1472-490X
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D002627:Chemistry, Physical; D004220:Disulfides / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D018030:Silver Compounds / Q000737:chemistry
chemical_list: C000610544:3-pentafluorosulfanyl-pyridin-2-one; C000610542:3-pentafluorosulfanyl-quinolin-2-one; C000610543:3-pentafluorosulfanyl-quinoline; D004220:Disulfides; D007659:Ketones; D011728:Pyridones; D011804:Quinolines; D015363:Quinolones; D018030:Silver Compounds; C105022:silver fluoride; D005459:Fluorides
keywords: aldol reactions; boron; heterocycles; pentafluorosulfanyl; physicochemical properties