Phosphines featuring a hexafluorocyclopentene skeleton: Synthesis, coordination properties, and applications for Lewis-acidic transition-metal catalysts

Results in Chemistry - Tập 1 - Trang 100008 - 2019
Tomohiro Agou1, Nao Wada1, Momoko Komatsu1, Miki Nohara1, Yoshiyuki Mizuhata2, Norihiro Tokitoh2, Takaaki Hosoya1, Hiroki Fukumoto1, Toshio Kubota1
1Department of Quantum Beam Science, Graduate School of Science, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki 316-8511, Japan
2Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan

Tài liệu tham khảo

Andersen, 2001, 2-Furyl phosphines as ligands for transition-metal-mediate organic synthesis, Chem. Rev., 101, 997, 10.1021/cr000024o Tinnermann, 2018, N-arylpyridiniophosphines: synthesis, structure, and applications in Au(I) catalysis, ACS Catal., 8, 10457, 10.1021/acscatal.8b03271 Kozma, 2014, Coordination chemistry of cyclopropenylidene-stabilized phosphenium cations: synthesis and reactivity of Pd and Pt complexes, Chem. Eur. J., 20, 2208, 10.1002/chem.201303686 Tinnermann, 2014, Synthesis, structure, and applications of pyridiniophosphines, Angew. Chem. Int. Ed., 53, 8732, 10.1002/anie.201401073 Carreras, 2012, Exploiting the π-acceptor properties of carbene-stabilized phosphorus centered trications [L3P]3+: applications in Pt(II) catalysis, J. Am. Chem. Soc., 134, 16753, 10.1021/ja306947m Petuškova, 2011, Synthesis, structure, and reactivity of carbene-stabilized phospho-rus(III)-centered trications [L3P]3+, J. Am. Chem. Soc., 133, 20758, 10.1021/ja210223s Ozawa, 2016, PNP-pincer-type phosphaalkene complexes of late transition metals, Chem. Rec., 16, 2314, 10.1002/tcr.201600054 Ozawa, 2004, Synthesis and catalytic properties of diphosphinidenecyclobutene-coordinated palladium and platinum complexes, C. R. Chim., 7, 747, 10.1016/j.crci.2004.05.001 Ozawa, 2006, Catalytic applications of transition-metal complexes bearing diphos-phinidenecyclobutenes (DPCB), Dalton Trans., 4987, 10.1039/b610327h Ozawa, 2009, Structures and catalytic properties of diphosphinidenecyclobutene complexes, J. Synth. Org. Chem., Jpn., 67, 529, 10.5059/yukigoseikyokaishi.67.529 Ito, 2017, Stereoselective catalytic synthesis of alkynylated phosphaethenes leading to activation-free gold catalysis, Eur. J. Org. Chem., 6889, 10.1002/ejoc.201701259 Ito, 2016, Dynamic chirality control of tropos DPCB-digold skeleton by chiral binaphthyldicarboxylate, Chem. Asian J., 11, 823, 10.1002/asia.201501326 Ito, 2014, π-Extended DPCB for activation-free homogeneous gold catalysis, ChemCatChem, 6, 2292, 10.1002/cctc.201402158 Freytag, 2006, Coordination behavior of sterically protected phosphaalkenes on the AuCl moiety leading to catalytic 1,6-enyne cycloisomerization, Chem. Asian J., 1, 693, 10.1002/asia.200600155 Akahori, 2018, Synthesis and photodynamics of tetragermatetrathia[8]circulene, Org. Lett., 20, 304, 10.1021/acs.orglett.7b03764 Mitsudo, 2017, Rh-catalyzed dehydrogenative cyclization leading to benzosilolothiophene derivatives via Si-H/C-H bond cleavage, Org. Lett., 19, 2564, 10.1021/acs.orglett.7b00878 Takeuchi, 2018, Synthesis of multisubstituted azatriphenylenes by iridium-catalyzed [2+2+2] cycloaddition of biaryl-linked diynes with nitriles, J. Organomet. Chem., 83, 1852, 10.1021/acs.joc.7b02784 Korenaga, 2011, Application of 2,6-bis(trifluoromethyl)-4-pyridyl phosphanes: the most electron-poor aryl phosphanes with moderate bulkiness, Angew. Chem. Int. Ed., 50, 10703, 10.1002/anie.201104588 Korenaga, 2018, Computationally-led ligand modification using interplay between theory and experiments: highly active rhodium catalyst controlled by electronic effects and CH-π interactions, Adv. Synth. Catal., 360, 322, 10.1002/adsc.201701191 Fernández, 2017, (I)-catalyzed intramolecular hydrocarbonation of alkenes: efficient access to cyclic systems bearing quaternary stereocenters, Angew. Chem. Int. Ed., 56, 9541, 10.1002/anie.201705105 Crisenza, 2015, Branch-selective alkene hydroarylation by cooperative destabilization: iridium-catalyzed ortho-alkylation of acetanilides, Angew. Chem. Int. Ed., 54, 14866, 10.1002/anie.201506581 Crisenza, 2014, Branch-selective, iridium-catalyzed hydroarylation of monosubstituted alkenes via a cooperative destabilization strategy, J. Am. Chem. Soc., 136, 10258, 10.1021/ja505776m Kim, 2017, Flexible tetrahydropyran synthesis from homopropargylic alcohols using sequential Pd-Au catalysis, Org. Lett., 19, 242, 10.1021/acs.orglett.6b03532 Nielsen, 2014, Design for the reductive elimination of ArCF3 from a small bite angle PdII complex: remarkable effect of a perfluoroalkyl phosphine, Angew. Chem. Int. Ed., 53, 5903, 10.1002/anie.201400837 Hussein, 2019, Filling a niche in “Ligand Space” with bulky, electron-poor phosphorus(III) alkoxides, Chem. Eur. J., 25, 2262, 10.1002/chem.201804805 Gotsu, 2018, Fluorine-containing dibenzo-anthracene and benzoperylene-type polycyclic aromatic hydrocarbons: synthesis, structure, and basic chemical properties, Molecules, 23, 3337, 10.3390/molecules23123337 Agou, 2018, A straight-forward synthesis of polyfluorinated furan derivatives and their property, Asian J. Org. Chem., 7, 2484, 10.1002/ajoc.201800454 Kataoka, 2018, Effective synthesis of fluorine-containing phenanthrene bearing hydroxyl group using Mallory reaction and its application for fluorinated polymers, J. Fluor. Chem., 218, 84, 10.1016/j.jfluchem.2018.11.017 Fukumoto, 2017, efficient synthesis of fluorinated phenanthrene monomers using Mallory reaction and their copolymerization, Macromolecules, 50, 865, 10.1021/acs.macromol.6b02151 Agou, 2018, Syntheses and structures of d10 coinage metal complexes of electron-accepting phosphine ligands featuring a 3,3,4,4,5,5-hexafluorocyclopentene framework, Inorg. Chem., 57, 9105, 10.1021/acs.inorgchem.8b01111 Cullen, 1969, Characterization of [3,3,4,4-tetrafluoro-1,2-bis(dimethylarsino)cyclobutene] diiron hexacarbonyl and related complexes, Inorg. Chem., 8, 95, 10.1021/ic50071a023 Stockel, 1968, Reactions of 1,2-dichlorohexafluorocyclopentene with secondary phosphines, Can. J. Chem., 46, 2625, 10.1139/v68-428 Allen, 1982, The chemistry of heteroarylphosphorus compounds. Part 15. Phosphorus-31 nuclear magnetic resonance studies of the donor properties of heteroarylphosphines towards selenium and platinum(II), J. Chem. Soc. Dalton Trans., 51, 10.1039/dt9820000051 Beckmann, 2011, Is the 1JPSe coupling constant a reliable probe for the basicity of phosphines? A 31P NMR study, Phosphorus Sulfur Silicon Relat. Elem., 186, 2061, 10.1080/10426507.2010.547892 Juanatey, 1999, cis-[1,2-Bis(diphenylphosphino)ethene]dichloropalladium(II) bis(trichloromethane) solvate, Acta Cryst, C55 Ghosh, 2011, Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol, J. Organomet. Chem., 76, 500, 10.1021/jo101995g Oliver-Meseguer, 2012, Small gold clusters formed in solution give reaction turnovers of 107 at room temperature, Science, 338, 1452, 10.1126/science.1227813 Sheldrick, 2015, Crystal structure refinement with SHELXL, Acta Cryst, 3 Frisch, 2016