{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T15:19:42Z","timestamp":1788362382183,"version":"build-2803163510"},"reference-count":141,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2005,1,13]],"date-time":"2005-01-13T00:00:00Z","timestamp":1105574400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2005,2,18]]},"abstract":"Abstract<\/jats:title>Reactions of [(\u03b75<\/jats:sup>\u2010C5<\/jats:sub>H5<\/jats:sub>)Ru(PR\u20323<\/jats:sub>)2<\/jats:sub>(Cl)] with NaBArF<\/jats:sub> [BArF<\/jats:sub>\u2212<\/jats:sup>=B{3,5\u2010[C6<\/jats:sub>H3<\/jats:sub>(CF3<\/jats:sub>)2<\/jats:sub>]}4<\/jats:sub>\u2212<\/jats:sup>; PR\u20323<\/jats:sub>=PEt3<\/jats:sub> or 1\/2Et2<\/jats:sub>PCH2<\/jats:sub>CH2<\/jats:sub>PEt2<\/jats:sub> (depe)] and PR2<\/jats:sub>H (R=Ph, a<\/jats:bold>; t<\/jats:italic>Bu, b<\/jats:bold>; Cy, c<\/jats:bold>) in C6<\/jats:sub>H5<\/jats:sub>F, or of related cationic Ru(N2<\/jats:sub>) complexes with PR2<\/jats:sub>H in C6<\/jats:sub>H5<\/jats:sub>F, gave the secondary phosphine complexes [(\u03b75<\/jats:sup>\u2010C5<\/jats:sub>H5<\/jats:sub>)Ru(PR\u20323<\/jats:sub>)2<\/jats:sub>(PR2<\/jats:sub>H)]+<\/jats:sup> BArF<\/jats:sub>\u2212<\/jats:sup> (PR\u20323<\/jats:sub>=PEt3<\/jats:sub>, 3\u2009a<\/jats:bold>\u2013c<\/jats:bold>; 1\/2depe, 4\u2009a<\/jats:bold>,b<\/jats:bold>) in 65\u201391\u2009% yields. Additions of t<\/jats:italic>BuOK (3\u2009a<\/jats:bold>, 4\u2009a<\/jats:bold>; [D6<\/jats:sub>]acetone) or NaN(SiMe3<\/jats:sub>)2<\/jats:sub> (3\u2009b<\/jats:bold>,c<\/jats:bold>, 4\u2009b<\/jats:bold>; [D8<\/jats:sub>]THF) gave the title complexes [(\u03b75<\/jats:sup>\u2010C5<\/jats:sub>H5<\/jats:sub>)Ru(PEt3<\/jats:sub>)2<\/jats:sub>(PR2<\/jats:sub>)] (5\u2009a<\/jats:bold>\u2013c<\/jats:bold>) and [(\u03b75<\/jats:sup>\u2010C5<\/jats:sub>H5<\/jats:sub>)Ru(depe)(PR2<\/jats:sub>)] (6\u2009a<\/jats:bold>,b<\/jats:bold>) in high spectroscopic yields. These complexes were rapidly oxidized in air; with 5\u2009a<\/jats:bold>, [(\u03b75<\/jats:sup>\u2010C5<\/jats:sub>H5<\/jats:sub>)Ru(PEt3<\/jats:sub>)2<\/jats:sub>{P(\uf8feO)Ph2<\/jats:sub>}] was isolated (>99\u2009%). The reaction of 5\u2009a<\/jats:bold> and elemental selenium yielded [(\u03b75<\/jats:sup>\u2010C5<\/jats:sub>H5<\/jats:sub>)Ru(PEt3<\/jats:sub>)2<\/jats:sub>{P(\uf8feSe)Ph2<\/jats:sub>}] (70\u2009%); selenides from 5\u2009c<\/jats:bold> and 6\u2009a<\/jats:bold> were characterized in situ. Competitive deprotonation reactions showed that 5\u2009a<\/jats:bold> is more basic than the rhenium analog [(\u03b75<\/jats:sup>\u2010C5<\/jats:sub>H5<\/jats:sub>)Re(NO)(PPh3<\/jats:sub>)(PPh2<\/jats:sub>)], and that 6\u2009b<\/jats:bold> is more basic than Pt<\/jats:italic>Bu3<\/jats:sub> and P(i<\/jats:italic>PrNCH2<\/jats:sub>CH2<\/jats:sub>)3<\/jats:sub>N. The latter is one of the most basic trivalent phosphorus compounds [pK<\/jats:italic>a<\/jats:sub>(acetonitrile) 33.6]. Complexes 5\u2009a<\/jats:bold>\u2013c<\/jats:bold> and 6\u2009b<\/jats:bold> are effective ligands for Pd(OAc)2<\/jats:sub>\u2010catalyzed Suzuki coupling reactions: 6\u2009b<\/jats:bold> gave a catalyst nearly as active as the benchmark organophosphine Pt<\/jats:italic>Bu3<\/jats:sub>; 5\u2009a<\/jats:bold>, with a less bulky and electron\u2010rich PR2<\/jats:sub> moiety, gave a less active catalyst. The reaction of 5\u2009a<\/jats:bold> and [(\u03b73<\/jats:sup>\u2010C3<\/jats:sub>H5<\/jats:sub>)Pd(NCPh)2<\/jats:sub>]+<\/jats:sup>\u2009BF4<\/jats:sub>\u2212<\/jats:sup> gave the bridging phosphido complex [(\u03b75<\/jats:sup>\u2010C5<\/jats:sub>H5<\/jats:sub>)Ru(PEt3<\/jats:sub>)2<\/jats:sub>(PPh2<\/jats:sub>)Pd(NCPh)(\u03b73<\/jats:sup>\u2010C3<\/jats:sub>H5<\/jats:sub>)]+<\/jats:sup>\u2009BArF<\/jats:sub>\u2212<\/jats:sup> in approximately 90\u2009% purity. The crystal structure of 4\u2009a<\/jats:bold> is described, as well as substitution reactions of 3\u2009b<\/jats:bold> and 4\u2009b<\/jats:bold>.<\/jats:p>","DOI":"10.1002\/chem.200400925","type":"journal-article","created":{"date-parts":[[2005,1,13]],"date-time":"2005-01-13T14:22:51Z","timestamp":1105626171000},"page":"1402-1416","source":"Crossref","is-referenced-by-count":38,"title":["Generation and Reactions of Ruthenium Phosphido Complexes [(\u03b75<\/sup>\u2010C5<\/sub>H5<\/sub>)Ru(PR\u20323<\/sub>)2<\/sub>(PR2<\/sub>)]: Remarkably High Phosphorus Basicities and Applications as Ligands for Palladium\u2010Catalyzed Suzuki Cross\u2010Coupling Reactions"],"prefix":"10.1002","volume":"11","author":[{"given":"Jos\u00e9","family":"Giner Planas","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Frank","family":"Hampel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J. 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Gladysz unpublished results."},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/b207963c"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00216a015"},{"key":"e_1_2_7_35_2","first-page":"25","volume":"18","author":"Caulton K. G.","year":"1994","journal-title":"New J. 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However for the types of compounds anions and solvents used in this study any effect of the anion upon the equilibrium should be small (see ref. [29])."},{"key":"e_1_2_7_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja994428d"},{"key":"e_1_2_7_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00003a022"},{"key":"e_1_2_7_86_2","first-page":"3","volume":"37","author":"Verkade J. G.","year":"2004","journal-title":"Aldrichimica Acta"},{"key":"e_1_2_7_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo000427o"},{"key":"e_1_2_7_88_2","doi-asserted-by":"publisher","DOI":"10.1080\/00945718408055896"},{"key":"e_1_2_7_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00040a067"},{"key":"e_1_2_7_90_2","unstructured":"\u00a0"},{"key":"e_1_2_7_91_2","first-page":"386","volume-title":"in Comprehensive Organometallic Chemistry","author":"Maitlis P. 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However the BArF\u2212salt appeared to be much more stable."},{"key":"e_1_2_7_102_2","unstructured":"\u00a0"},{"key":"e_1_2_7_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00435a017"},{"key":"e_1_2_7_104_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2002.346"},{"key":"e_1_2_7_105_2","unstructured":"\u00a0"},{"key":"e_1_2_7_106_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01290a009"},{"key":"e_1_2_7_107_2","doi-asserted-by":"publisher","DOI":"10.1002\/mrc.1270150110"},{"key":"e_1_2_7_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/om001034i"},{"key":"e_1_2_7_109_2","unstructured":"A. Nawara unpublished results."},{"key":"e_1_2_7_110_2","unstructured":"\u00a0"},{"key":"e_1_2_7_111_2","unstructured":"For some dibridgehead diphosphines that are also more basic than PtBu3 see ref. [45b]. These also give conjugate acids with a hypervalent phosphorus atom;"},{"key":"e_1_2_7_112_2","doi-asserted-by":"publisher","DOI":"10.1039\/b008903f"},{"key":"e_1_2_7_113_2","doi-asserted-by":"publisher","DOI":"10.1080\/13583149512331338275"},{"key":"e_1_2_7_114_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00116a014"},{"key":"e_1_2_7_115_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo971176v"},{"key":"e_1_2_7_116_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(97)00143-5"},{"key":"e_1_2_7_117_2","doi-asserted-by":"publisher","DOI":"10.1021\/om980340h"},{"key":"e_1_2_7_118_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00059a071"},{"key":"e_1_2_7_119_2","unstructured":"Tentative assignment; this coupling has been attributed both to fluorine and boron in the literature."},{"key":"e_1_2_7_120_2","doi-asserted-by":"publisher","DOI":"10.1039\/DT9960000377"},{"key":"e_1_2_7_121_2","unstructured":"FAB 3\u2010NBA:m\/zfor the most intense peak of the isotope envelope; relative intensities (%) are for the specified mass range."},{"key":"e_1_2_7_122_2","unstructured":"\u00a0"},{"key":"e_1_2_7_123_2","unstructured":"This assignment and\/or coupling constant was determined from homodecoupling and1H\u20131H COSY experiments;"},{"key":"e_1_2_7_124_2","unstructured":"The allyl protons are numbered as H1H2C\uf8ffCH5\uf8ffCH3H4 with H1and H4synto H5 and H2and H3antito H5;"},{"key":"e_1_2_7_125_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1169(99)00139-9"},{"key":"e_1_2_7_126_2","unstructured":"Simulation of the31P spectrum with gNMR shows that the2J(P P) value for the PEt3ligands is <2.0 Hz."},{"key":"e_1_2_7_127_2","first-page":"343","volume":"28","author":"Tatsumo Y.","year":"1990","journal-title":"Inorg. Synth."},{"key":"e_1_2_7_128_2","unstructured":"The \uf8feCHCH31H NMR signal is resolved in CDCl3: 1.88 ppm (br\u2009dd 3J(H H)=6.4 Hz 4J(H P)=1.2 Hz 3\u2009H)."},{"key":"e_1_2_7_129_2","unstructured":"A DEPT experiment confirmed that this signal arises from a methyl group."},{"key":"e_1_2_7_130_2","unstructured":"\u00a0"},{"key":"e_1_2_7_131_2","unstructured":"\u201cCollect\u201d data collection software B. V. Nonius 1998;"},{"key":"e_1_2_7_132_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0076-6879(97)76066-X"},{"key":"e_1_2_7_133_2","unstructured":"G. M. Sheldrick SHELX\u201097 Program for refinement of crystal structures University of G\u00f6ttingen 1997."},{"key":"e_1_2_7_134_2","volume-title":"International Tables for X\u2010ray Crystallography","author":"Cromer D. T.","year":"1974"},{"key":"e_1_2_7_135_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767383001762"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200400925","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200400925","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:45:48Z","timestamp":1760273148000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200400925"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005,2,14]]},"references-count":141,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2005,2,18]]}},"alternative-id":["10.1002\/chem.200400925"],"URL":"https:\/\/doi.org\/10.1002\/chem.200400925","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2005,2,14]]}}}