652-31-3Relevant articles and documents
Catalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH4
Schoch, Timothy D.,Mondal, Mukulesh,Weaver, Jimmie D.
supporting information, p. 1588 - 1593 (2021/03/03)
Presented is an economical means of removing fluorine from various highly fluorinated arenes using NaBH4. The procedure was adapted for different classes of perfluoroarenes. A novel isomer of an emerging class of organic dyes based on the carbazole phthalonitrile motif was succinctly synthesized in two steps from tetrafluorophthalonitrile, demonstrating the utility of the hydrodefluorination procedure. Initial exploration of the dye shows it to be photoactive and capable of facilitating contrathermodynamic styrenoid E/Z isomerization.
Mn(i) organometallics containing the iPr2P(CH2)2PiPr2 ligand for the catalytic hydration of aromatic nitriles
Gardu?o, Jorge A.,Arévalo, Alma,Flores-Alamo, Marcos,García, Juventino J.
, p. 2606 - 2616 (2018/05/30)
The first example of a homogeneous hydration of aromatic nitriles catalyzed by manganese molecular compounds is reported. The Mn(i) organometallics fac-[(CO)3Mn(dippe)(Z)]1-nX1-n (n = 0, 1; Z = Br, OTf, PhCN; X = OTf) were synthesized and characterized, and their reactivity was studied. The species fac-[(CO)3Mn(dippe)(OTf)] (2) was used as a catalyst precursor for the selective hydration of benchmark benzonitrile (2 mol% 2, THF/H2O 1:2 v/v, 18 h, 100 °C) to produce benzamide in 90% isolated yield. A series of (hetero)aromatic nitriles were hydrated to synthesize the corresponding amides in very good to excellent yields (88-94%). Isotopic labeling studies accounted for a proton transfer as the rate-determining step.
Synthesis and catalytic applications of ruthenium(ii)-phosphino-oxime complexes
Francos, Javier,Menéndez-Rodríguez, Lucía,Tomás-Mendivil, Eder,Crochet, Pascale,Cadierno, Victorio
, p. 39044 - 39052 (2016/06/01)
In this work, the preparation of the first ruthenium complexes containing a phosphino-oxime ligand is presented. Thus, the reaction of cis-[RuCl2(DMSO)4] (3) with 2.4 equivalents of 2-Ph2PC6H4CH=NOH (1) in refluxing THF led to the clean formation of the octahedral ruthenium(ii) derivative cis,cis,trans-[RuCl2{κ2-(P,N)-2-Ph2PC6H4CH=NOH}2] (5), whose structure was unambiguously confirmed by means of a single-crystal X-ray diffraction study. Complex 5 could also be synthesized from the reaction of the dimer [{RuCl(μ-Cl)(η6-p-cymene)}2] (4) with an excess of 1 in refluxing toluene. Treatment of 4 with 2 equivalents of 1, in CH2Cl2 at r.t., allowed also the preparation of the half-sandwich Ru(ii) derivative [RuCl{κ2-(P,N)-2-Ph2PC6H4CH=NOH}(η6-p-cymene)][PF6] (6). In addition, complexes 5 and 6 proved to be active catalysts for the rearrangement of aldoximes to primary amides, as well as for the α-alkylation/reduction of acetophenones with primary alcohols, with the former showing the best performances in both processes.
