{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T15:14:07Z","timestamp":1790694847592,"version":"4.1.0"},"reference-count":100,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2014,4,22]],"date-time":"2014-04-22T00:00:00Z","timestamp":1398124800000},"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":[[2014,5,19]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We report the first success in the gold\u2010catalyzed oxoarylations of nitriles with pyridine\u2010derived <jats:italic>N<\/jats:italic>\u2010oxides using gold carbenes as initiators. These oxoarylations were also achieved satisfactorily in intermolecular three\u2010component oxidations, including diverse alkenyldiazo esters, nitriles, and pyridine\u2010based oxides.<\/jats:p>","DOI":"10.1002\/anie.201403015","type":"journal-article","created":{"date-parts":[[2014,4,22]],"date-time":"2014-04-22T12:40:57Z","timestamp":1398170457000},"page":"5444-5448","source":"Crossref","is-referenced-by-count":94,"title":["Gold\u2010Catalyzed 1,2\u2010Oxoarylations of Nitriles with Pyridine\u2010Derived Oxides"],"prefix":"10.1002","volume":"53","author":[{"given":"Somnath Narayan","family":"Karad","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rai\u2010Shung","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,4,22]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"Review:"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201100148"},{"key":"e_1_2_2_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100148"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar400181x"},{"key":"e_1_2_2_4_2","unstructured":"\u00a0"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja100041e"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1033952"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201007624"},{"key":"e_1_2_2_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201007624"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300518"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo301381z"},{"key":"e_1_2_2_10_2","unstructured":"\u00a0"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1072614"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2029188"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja307948m"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201210313"},{"key":"e_1_2_2_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201210313"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201108027"},{"key":"e_1_2_2_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201108027"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102581"},{"key":"e_1_2_2_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102581"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304700"},{"key":"e_1_2_2_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304700"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201208305"},{"key":"e_1_2_2_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201208305"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301015"},{"key":"e_1_2_2_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301015"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201303016"},{"key":"e_1_2_2_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303016"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304813"},{"key":"e_1_2_2_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304813"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4085385"},{"key":"e_1_2_2_23_2","unstructured":"\u00a0"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja070789e"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol9020578"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004647"},{"key":"e_1_2_2_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004647"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja401343p"},{"key":"e_1_2_2_28_2","unstructured":"\u00a0"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja208150d"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol302621z"},{"key":"e_1_2_2_31_2","unstructured":"\u00a0"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol990522n"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja02246a012"},{"key":"e_1_2_2_34_2","unstructured":"\u00a0"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(64)83021-5"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(58)80001-0"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00170a044"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00932a028"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00890a032"},{"key":"e_1_2_2_40_2","unstructured":"See 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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_68_2","unstructured":"For catalytic [3+2]\u2010cycloadditions between nitriles and \u03b1\u2010oxo or \u03b1\u2010imino carbene species see Ref.\u2005[3b] and selected examples:"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol302102h"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)90396-5"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1992.2197"},{"key":"e_1_2_2_72_2","unstructured":"For synthesis of pyrrole compounds from the [3+2] cycloadditions of nitriles and alkenylmetal carbenes see:"},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol400062w"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201300346"},{"key":"e_1_2_2_75_2","unstructured":"For a nucleophilic addition at C3 of alkenylgold carbenes see: Ref.\u2005[16b] and"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja209980d"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201203217"},{"key":"e_1_2_2_78_2","unstructured":"For the same regioselectivity of alkenylrhodium carbenes see selected examples:"},{"key":"e_1_2_2_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201305539"},{"key":"e_1_2_2_79_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201305539"},{"key":"e_1_2_2_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja207664r"},{"key":"e_1_2_2_81_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201203962"},{"key":"e_1_2_2_81_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201203962"},{"key":"e_1_2_2_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201204047"},{"key":"e_1_2_2_82_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204047"},{"key":"e_1_2_2_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol300632p"},{"key":"e_1_2_2_84_2","unstructured":"We attempted to realize an oxoarylation reaction with the nitrilium intermediatesFgenerated from diphenylmethanol and acetonitrile (10\u2005equiv) according to Hashmi\u2019s report[22][Eq.\u2005(3)]. We obtained the amide10and ether11in 53 and 36\u2009% yield respectively without any oxidant. In the presence of 8\u2010methylquinolineN\u2010oxide (1.2\u2005equiv) we obtained no oxoarylation product in tractable amount [Eq.\u2005(4)] whereas species10and11were still formed. Accordingly not every nitrilium species can be used in the oxoarylation reaction."},{"key":"e_1_2_2_85_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201000779"},{"key":"e_1_2_2_86_2","unstructured":"Unsubstituted pyridine and quinolineN\u2010oxides were inapplicable substrates for the reaction is Tables\u20052\u20133 because the released pyridine and quinoline were expected to poison gold catalyst."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201403015","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201403015","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T16:01:27Z","timestamp":1697472087000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201403015"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,4,22]]},"references-count":100,"journal-issue":{"issue":"21","published-print":{"date-parts":[[2014,5,19]]}},"alternative-id":["10.1002\/anie.201403015"],"URL":"https:\/\/doi.org\/10.1002\/anie.201403015","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,4,22]]}}}