{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T23:18:13Z","timestamp":1791069493121,"version":"4.1.0"},"reference-count":73,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2012,2,29]],"date-time":"2012-02-29T00:00:00Z","timestamp":1330473600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2012,4,10]]},"DOI":"10.1002\/anie.201200486","type":"journal-article","created":{"date-parts":[[2012,2,29]],"date-time":"2012-02-29T13:43:42Z","timestamp":1330523022000},"page":"3686-3690","source":"Crossref","is-referenced-by-count":116,"title":["Cyanosilylation of Carbonyl Compounds with Trimethylsilyl Cyanide Catalyzed by an Yttrium\u2010Pillared Silicotungstate Dimer"],"prefix":"10.1002","volume":"51","author":[{"given":"Yuji","family":"Kikukawa","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kosuke","family":"Suzuki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Midori","family":"Sugawa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomohisa","family":"Hirano","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Keigo","family":"Kamata","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazuya","family":"Yamaguchi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Noritaka","family":"Mizuno","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2012,2,29]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9902906"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300604"},{"key":"e_1_2_2_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300604"},{"key":"e_1_2_2_4_2","unstructured":"For 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Supporting Information for more details) see:"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200802536"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.200800183"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/b718462j"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200601791"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462424"},{"key":"e_1_2_2_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462424"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200606124"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0482083"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.66.2016"},{"key":"e_1_2_2_23_2","unstructured":"For asymmetric cyanosilylation see:"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2007.09.010"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300415"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020315)114:6<1051::AID-ANGE1051>3.0.CO;2-Z"},{"key":"e_1_2_2_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020315)41:6<1009::AID-ANIE1009>3.0.CO;2-F"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0163772"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja983895c"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo201864e"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100319"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja101208s"},{"key":"e_1_2_2_32_2","unstructured":"\u00a0"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/0010-8545(95)01141-B"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0360-0564(08)60041-3"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470166482.ch3"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr960395y"},{"key":"e_1_2_2_37_2","volume-title":"Catalysis by Polyoxometalates","author":"Kozhevnikov I. V.","year":"2002"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201100025"},{"key":"e_1_2_2_39_2","unstructured":"The cyanosilylation of1\u2009ahardly proceeded in the presence of a \u22124\u2010charged POM TBA4[\u03b1\u2010SiW12O40] (Table\u2005S2)."},{"key":"e_1_2_2_40_2","unstructured":"The formation of trimethylsilanol was also confirmed by GC\u2010MS analysis of the solution."},{"key":"e_1_2_2_41_2","unstructured":"The formation of trimethylsilanol was hardly observed in the presence of excess amounts of carbonyl compounds (catalytic turnover conditions)."},{"key":"e_1_2_2_42_2","unstructured":"For several efficient functional\u2010group transformations catalyzed by Lewis acidic POMs see:"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200600364"},{"key":"e_1_2_2_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200600364"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700010"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201000411"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201000218"},{"key":"e_1_2_2_47_2","unstructured":"We have reported similar in\u2005situ prepared catalysts such as TBA8[{Zn(OH2)(\u03bc3\u2010OH)}2{Zn(OH2)2}2(\u03b3\u2010HSiW10O36)2]\u22c59\u2009H2O (Zn(acac)2+SiW10)[11a]and TBA8[Ag4(DMSO)2(\u03b3\u2010H2SiW10O36)2]\u22c52\u2009DMSO\u22c52\u2009H2O (AgOAc+SiW10) (DMSO=dimethyl sulfoxide OAc=acetate):[11b]"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201001468"},{"key":"e_1_2_2_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201001468"},{"key":"e_1_2_2_49_2","unstructured":"Y. Kikukawa Y. Kuroda K. Yamaguchi N. Mizuno Angew. Chem.2012 DOI:;Angew. Chem. Int. Ed.2012 DOI:."},{"key":"e_1_2_2_50_2","unstructured":"The IR spectrum ofY2was very similar to that ofY2\u2019(Figure\u2005S8). Although the complete structural determination ofY2by X\u2010ray crystallographic analysis has so far been unsuccessful because of the severe disorder around the yttrium centers and TBA molecules Y2was determined to be a dimer of [\u03b3\u2010SiW10O36]8\u2212pillared by two yttrium atoms and the structure was almost identical to that ofY2\u2032. In addition the positive\u2010ion CSI\u2010MS analysis ofY2\u2032in acetonitrile showed only the sets of signals resulting from the POM [(SiYW10O36)2]10\u2212(Figure\u2005S9). All these results show that the anion structures ofY2andY2\u2032are intrinsically identical and the difference between them is the number of TBA cations."},{"key":"e_1_2_2_51_2","unstructured":"CCDC\u2005860121 (compoundY2\u2032) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_2_52_2","unstructured":"The stretching vibration of the C\uf8feO bond of coordinated acetone molecules on the yttrium centers was observed at 1696\u2005cm\u22121(that of non\u2010coordinated acetone: 1715\u2005cm\u22121) thus suggesting that acetone is electrophilically activated on the yttrium centers."},{"key":"e_1_2_2_53_2","volume-title":"The Hydrogen Bond","author":"Pimentel G. C.","year":"1960"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic960101r"},{"key":"e_1_2_2_55_2","unstructured":"\u00a0"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1039\/j19710001836"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja992105b"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20011105)113:21<4155::AID-ANGE4155>3.0.CO;2-R"},{"key":"e_1_2_2_58_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20011105)40:21<4031::AID-ANIE4031>3.0.CO;2-8"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.75.1275"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic0350842"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200400774"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.200800240"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.poly.2008.02.035"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1080\/00958972.2010.511666"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic102149c"},{"key":"e_1_2_2_66_2","unstructured":"The scope of cyanosilylation of various ketones was examined withY2(Table\u20051) because of the very low solubility ofY2\u2032in 1 2\u2010dichloroethane (below 0.05\u2005mM). The cyanosilylation of aldehyde1\u2009owas carried out withY2\u2032(0.005\u2005mol\u2009%) in 1 2\u2010dichloroethane under the conditions described in Scheme\u20052. AlthoughY2\u2032was partially insoluble under this conditions 2\u2009owas obtained in 78\u2009% yield."},{"key":"e_1_2_2_67_2","unstructured":"Competitive cyanosilylations of1\u2009band1\u2009dwith Sc(OTf)3(OTf=triflate) and MgO were carried out under the same reaction conditions. In the case of Sc(OTf)3 2\u2009band2\u2009dwere obtained in 70\u2009% and 27\u2009% yields respectively. MgO selectively gave2\u2009bin 79\u2009% yield along with a small amount of2\u2009d(2\u2009% yield). The ratio of the yields of2\u2009band2\u2009dwithY2(89\/9) was much higher than that with the homogeneous catalyst Sc(OTf)3(70\/27) and comparable to that with the heterogeneous catalyst MgO (79\/2)."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201200486","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201200486","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T19:21:13Z","timestamp":1697484073000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201200486"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,2,29]]},"references-count":73,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2012,4,10]]}},"alternative-id":["10.1002\/anie.201200486"],"URL":"https:\/\/doi.org\/10.1002\/anie.201200486","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,2,29]]}}}