56153-06-1Relevant articles and documents
Efficient protocol for the SO2F2-mediated deoxyfluorination of aliphatic alcohols
Epifanov, Maxim,Lai, Joey,Lee, Cayo,Sammis, Glenn M.,Wang, Cindy Xinyun
supporting information, (2021/09/28)
Alkyl fluorides are prevalent in both the pharmaceutical and agrochemical industries. As such, there has been significant interest over the past 40 years in the development of new synthetic methods to access these important fluorinated motifs. Herein we report the sulfuryl fluoride-mediated deoxyfluorination of alcohols using room temperature reaction conditions in only an hour. A wide range of primary aliphatic alcohols were efficiently converted to the corresponding fluoride in 46-70% isolated yields. Secondary alcohols were also effectively deoxyfluorinated in 50–92% yields. Chiral secondary alcohols were cleanly converted to the corresponding alkyl fluoride with only a minor deterioration of the enantioenrichment. A steroid derivative also underwent deoxyfluorination in 50% yield and 5.9:1 dr, with the major product resulting from net inversion of the stereocenter.
Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands
Taylor, Nicholas J.,Emer, Enrico,Preshlock, Sean,Schedler, Michael,Tredwell, Matthew,Verhoog, Stefan,Mercier, Joel,Genicot, Christophe,Gouverneur, Véronique
supporting information, p. 8267 - 8276 (2017/06/27)
Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.
Hypervalent Iodine-Based Activation of Triphenylphosphine for the Functionalization of Alcohols
Eljo, Jasmin,Carle, Myriam S.,Murphy, Graham K.
supporting information, p. 2871 - 2875 (2017/10/06)
The use of hypervalent iodine reagents as a general tool for the activation of PPh 3 and its application to the functionalization of alcohols is reported. Combination of PPh 3 with PhICl 2 or TolIF 2 gives dihalophosphoranes that are characterized by 31 P NMR, however, with PhIOAc 2, PhI(OTFA) 2, or the cyclic chloro(benzoyloxy)iodane, no phosphoranes were observed. Reaction of these iodanes with PPh 3 in the presence of primary, secondary, or tertiary alcohols results in either halogenation or acyl-transfer products in moderate to high yield.
Synthesis and evaluation of 18F-labeled ATP competitive inhibitors of topoisomerase II as probes for imaging topoisomerase II expression
Daumar, Pierre,Zeglis, Brian M.,Ramos, Nicholas,Divilov, Vadim,Sevak, Kuntal Kumar,Pillarsetty, Nagavarakishore,Lewis, Jason S.
, p. 769 - 781 (2015/01/16)
Type II topoisomerase (Topo-II) is an ATP-dependent enzyme that is essential in the transcription, replication, and chromosome segregation processes and, as such, represents an attractive target for cancer therapy. Numerous studies indicate that the respo
Antibacterial compound
-
, (2008/06/13)
A compound of formula (I) wherein R1 and R2 represent a hydrogen atom or an aryl, a heterocyclic, an alkyl or an alkenyl, which are optionally substituted, R3 represents a hydrogen atom or a hydroxyl and X1 and
