{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,7]],"date-time":"2026-02-07T17:36:33Z","timestamp":1770485793311,"version":"3.49.0"},"reference-count":105,"publisher":"Wiley","issue":"14","license":[{"start":{"date-parts":[[2016,2,25]],"date-time":"2016-02-25T00:00:00Z","timestamp":1456358400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","award":["UID\/QUI\/00100\/2013"],"award-info":[{"award-number":["UID\/QUI\/00100\/2013"]}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"crossref","award":["4861\/4-1 and 4-2"],"award-info":[{"award-number":["4861\/4-1 and 4-2"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2016,3,24]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The Br\u00f8nsted acid\u2010mediated reaction of unactivated alkynes with aryl sulfoxides leads to simultaneous hydration and intermolecular C\u2212C bond formation. This solvent\u2010 and metal\u2010free transformation directly delivers \u03b1\u2010arylated carbonyl compounds as the products of a formal hydrative arylation in an atom\u2010economical manner. The products bear useful synthetic handles for further functionalization.<\/jats:p>","DOI":"10.1002\/chem.201600432","type":"journal-article","created":{"date-parts":[[2016,2,26]],"date-time":"2016-02-26T04:17:18Z","timestamp":1456460238000},"page":"4727-4732","source":"Crossref","is-referenced-by-count":95,"title":["Br\u00f8nsted Acid\u2010Mediated Hydrative Arylation of Unactivated Alkynes"],"prefix":"10.1002","volume":"22","author":[{"given":"Daniel","family":"Kaiser","sequence":"first","affiliation":[{"name":"Faculty of Chemistry Institute of Organic Chemistry University of Vienna  W\u00e4hringer Strasse 38 1090 Vienna Austria"}]},{"given":"Lu\u00eds F.","family":"Veiros","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural Instituto Superior T\u00e9cnico Universidade de Lisboa  Av. Rovisco Pais 1 1049-001 Lisboa Portugal"}]},{"given":"Nuno","family":"Maulide","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Institute of Organic Chemistry University of Vienna  W\u00e4hringer Strasse 38 1090 Vienna Austria"}]}],"member":"311","published-online":{"date-parts":[[2016,2,25]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.188101401320"},{"key":"e_1_2_2_2_1","unstructured":"For reviews on the hydration of alkynes see:"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-966002"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0201068"},{"key":"e_1_2_2_5_2","first-page":"199","volume-title":"Science of Synthesis, Vol.\u200525","author":"Oestreich M.","year":"2007"},{"key":"e_1_2_2_6_1","unstructured":"\u00a0"},{"key":"e_1_2_2_7_2","first-page":"209","volume":"3","author":"Desgrez A.","year":"1894","journal-title":"Ann. Chim."},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500324"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2004-817749"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo962115k"},{"key":"e_1_2_2_11_1","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","first-page":"2175","author":"Olivi N.","year":"2004","journal-title":"Synlett"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.05.155"},{"key":"e_1_2_2_14_2","first-page":"1777","author":"Tsuchimoto T.","year":"2000","journal-title":"Synlett"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00008a058"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19991004)38:19<2902::AID-ANIE2902>3.0.CO;2-2"},{"key":"e_1_2_2_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19991004)111:19<3083::AID-ANGE3083>3.0.CO;2-Q"},{"key":"e_1_2_2_17_1","unstructured":"\u00a0"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01270a061"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.15227\/orgsyn.035.0001"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01366a026"},{"key":"e_1_2_2_21_1","unstructured":"\u00a0"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200800666"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201200580"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.06.015"},{"key":"e_1_2_2_25_1","unstructured":"\u00a0"},{"key":"e_1_2_2_26_2","first-page":"2436","volume":"31","author":"Vartanyan S. A.","year":"1961","journal-title":"Zh. Obshch. Khim."},{"key":"e_1_2_2_27_2","first-page":"815","volume":"17","author":"Shestakov G. K.","year":"1976","journal-title":"Kinet. Catal."},{"key":"e_1_2_2_28_1","unstructured":"\u00a0"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00157a005"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00078a056"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/om020011w"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo961740m"},{"key":"e_1_2_2_33_1","unstructured":"\u00a0"},{"key":"e_1_2_2_34_2","first-page":"324","volume":"18","author":"Chin C. S.","year":"1997","journal-title":"Bull. Korean Chem. Soc."},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.12.010"},{"key":"e_1_2_2_36_1","unstructured":"\u00a0"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1351\/pac198355111845"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0619819"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)96302-0"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00020a024"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)80412-9"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol403684a"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201200420"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs401075z"},{"key":"e_1_2_2_45_1","unstructured":"\u00a0"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja036049x"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20021202)41:23<4563::AID-ANIE4563>3.0.CO;2-U"},{"key":"e_1_2_2_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20021202)114:23<4745::AID-ANGE4745>3.0.CO;2-S"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2003.11.011"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00011a058"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja809403e"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4GC01322K"},{"key":"e_1_2_2_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol050975u"},{"key":"e_1_2_2_53_1","unstructured":"\u00a0"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19981102)37:20<2867::AID-ANIE2867>3.0.CO;2-E"},{"key":"e_1_2_2_54_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19981016)110:20<3024::AID-ANGE3024>3.0.CO;2-0"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja046360u"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01480a036"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201404320"},{"key":"e_1_2_2_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201404320"},{"key":"e_1_2_2_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo070887i"},{"key":"e_1_2_2_59_1","unstructured":"For a review on alkyne addition to carbonyl groups see:"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200800776"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300579"},{"key":"e_1_2_2_61_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300579"},{"key":"e_1_2_2_62_2","volume-title":"Modern Carbonyl Chemistry","year":"2000"},{"key":"e_1_2_2_63_1","doi-asserted-by":"publisher","DOI":"10.1039\/jr9530003628"},{"key":"e_1_2_2_64_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)94470-3"},{"key":"e_1_2_2_65_1","unstructured":"\u00a0"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701449"},{"key":"e_1_2_2_66_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200701449"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja070789e"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301015"},{"key":"e_1_2_2_68_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301015"},{"key":"e_1_2_2_69_1","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201402055"},{"key":"e_1_2_2_70_1","unstructured":"For arylation reactions using diphenyl sulfoxide as the nucleophile see:"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201310865"},{"key":"e_1_2_2_71_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201310865"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol9020578"},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja401343p"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004647"},{"key":"e_1_2_2_74_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004647"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol401786d"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4017683"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300223"},{"key":"e_1_2_2_77_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201300223"},{"key":"e_1_2_2_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201405982"},{"key":"e_1_2_2_78_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201405982"},{"key":"e_1_2_2_79_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197803331"},{"key":"e_1_2_2_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19780900506"},{"key":"e_1_2_2_80_1","unstructured":"See the Supporting Information for optimization tables and further details."},{"key":"e_1_2_2_81_1","unstructured":"\u00a0"},{"key":"e_1_2_2_82_2","volume-title":"Density Functional Theory of Atoms and Molecules","author":"Parr R. G.","year":"1989"},{"key":"e_1_2_2_83_2","unstructured":"DFT calculations at the M06\u20132X\/[6-31+G(d p) PCM] level were performed using thegaussian09 package. A complete account of the computational details and the corresponding list of references are provided in the Supporting Information."},{"key":"e_1_2_2_84_1","unstructured":"Differences in the energy barriers of the [3 3] shift are also reflected in the geometries of the corresponding transition states. Thus in the case of reaction with PhS(O)Me the reactants have to move further along the reaction coordinate in order to attain the transition state corroborating a more difficult reaction in this case. See the Supporting Information for details."},{"key":"e_1_2_2_85_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201404380"},{"key":"e_1_2_2_86_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja506352b"},{"key":"e_1_2_2_87_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol2006874"},{"key":"e_1_2_2_88_1","unstructured":"AstrazenecaAB Astex Therapeutics Ltd. New Compounds.WO 2007\/058602A2 May 24 2007."},{"key":"e_1_2_2_89_1","first-page":"387","author":"Qi C.","year":"2011","journal-title":"Synthesis"},{"key":"e_1_2_2_90_1","unstructured":"For DNA-cleaving quinoxalines see:"},{"key":"e_1_2_2_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo020708r"},{"key":"e_1_2_2_92_2","first-page":"212","author":"Kazunobu T.","year":"2002","journal-title":"Chem. Commun."},{"key":"e_1_2_2_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm047705a"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201600432","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201600432","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201600432","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T10:01:50Z","timestamp":1760263310000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201600432"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,2,25]]},"references-count":105,"journal-issue":{"issue":"14","published-print":{"date-parts":[[2016,3,24]]}},"alternative-id":["10.1002\/chem.201600432"],"URL":"https:\/\/doi.org\/10.1002\/chem.201600432","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,2,25]]}}}