Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents
作者:Rui Guo、Xiaotian Qi、Hengye Xiang、Paul Geaneotes、Ruihan Wang、Peng Liu、Yi‐Ming Wang
DOI:10.1002/anie.202006278
日期:2020.9.14
available precursors remains a synthetic challenge. The metal‐free hydrofluorination of alkynes constitutes an attractive though elusive strategy for their preparation. Introduced here is an inexpensive and easily handled reagent that enables the development of simple and scalable protocols for the regioselective hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These
Designer HF-Based Fluorination Reagent: Highly Regioselective Synthesis of Fluoroalkenes and <i>gem</i>-Difluoromethylene Compounds from Alkynes
作者:Otome E. Okoromoba、Junbin Han、Gerald B. Hammond、Bo Xu
DOI:10.1021/ja508369z
日期:2014.10.15
hydrogen-bond acceptors (e.g., DMPU) can form stable complexes through hydrogen bonding. The DMPU/HF complex is a new nucleophilic fluorination reagent that has high acidity and is compatible with cationic metal catalysts. The gold-catalyzed mono- and dihydrofluorination of alkynes using the DMPU/HF complex yields synthetically important fluoroalkenes and gem-difluoromethlylene compounds regioselectively
Fluorinated phenylcyclopropylamines. Part 5: Effects of electron-withdrawing or -donating aryl substituents on the inhibition of monoamine oxidases A and B by 2-aryl-2-fluoro-cyclopropylamines
作者:Svenja Hruschka、Thomas C. Rosen、Shinichi Yoshida、Kenneth L. Kirk、Roland Fröhlich、Birgit Wibbeling、Günter Haufe
DOI:10.1016/j.bmc.2008.06.048
日期:2008.8
A series of racemic, diastereoisomeric aryl cyclopropylamines substituted with fluorine in the 2-position and electron-donating and electron-withdrawing groups on the aromatic ring have been prepared. These represent analogues of the classic MAO inhibitor tranylcypromine (trans-2-phenylcyclopropylamine, 1). Their activities as inhibitors of recombinant human liver monoamine oxidases A (MAO A) and B (MAO B) were determined. The trans-compounds were low micromolar inhibitors of both MAO A and MAO B with moderate MAO A selectivity while the less active cis-analogues were MAO B selective. In the trans-series, electron-withdrawing para-substituents increased the potency of MAO A inhibition while electron-donating groups such as methyl or methoxy had no influence on this activity. In contrast, aromatic ring substitution in the trans-series had essentially no effect on the inhibition of MAO B. The corresponding cis-compounds were shown to be 10-100 times less active against MAO A, while trans-and cis-compounds were quite similar in terms of inhibition of MAO B. The best MAO A/ MAO B selectivity (7: 1) in the trans-series was found for trans-2-fluoro-2-(para-trifluoromethylphenyl) cyclopropylamine (7d), while a 1: 27 selectivity was found for cis-2-fluoro-2-(para-fluorophenyl) cyclopropylamine (10c). These results are discussed in connection with the pK(a) and logD values, the mechanism of action of tranylcypromines, and the geometry of the active site of the enzymes. (C) 2008 Elsevier Ltd. All rights reserved.