{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,17]],"date-time":"2026-02-17T14:13:32Z","timestamp":1771337612529,"version":"3.50.1"},"reference-count":85,"publisher":"Wiley","issue":"22","license":[{"start":{"date-parts":[[2016,10,4]],"date-time":"2016-10-04T00:00:00Z","timestamp":1475539200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemCatChem"],"published-print":{"date-parts":[[2016,11,22]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Oxindoles and triazoles are very privileged frameworks in medicinal chemistry, and thus for the first time we report a catalytic asymmetric route that affords hitherto unknown families of <jats:italic>N<\/jats:italic>\u2010(1,2,3\u2010triazolmethyl)\u20103\u2010hydroxy\u20103\u2010phenyloxindoles using cheap biomass\u2010derived isatin precursors, rhodium catalysts (at only 3\u2005mol\u2009% loading), phosphane ligands, and arylboron reagents under mild conditions. We successfully obtained these compounds with good yields (up to 98\u2009% in the nonasymmetric series) and enantioselectivities in the range 84\u201395\u2009%\u2005<jats:italic>ee<\/jats:italic>. The reaction is very versatile, tolerant of a wide range of functional groups, and broad in reaction scope.<\/jats:p>","DOI":"10.1002\/cctc.201600901","type":"journal-article","created":{"date-parts":[[2016,8,31]],"date-time":"2016-08-31T15:11:45Z","timestamp":1472656305000},"page":"3518-3526","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Enantioselective Rhodium(I)\u2010Catalyzed Additions of Arylboronic Acids to <i>N<\/i>\u20101,2,3\u2010Triazole\u2010Isatin Derivatives: Accessing <i>N<\/i>\u2010(1,2,3\u2010Triazolmethyl)\u20103\u2010hydroxy\u20103\u2010aryloxindoles"],"prefix":"10.1002","volume":"8","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1697-7871","authenticated-orcid":false,"given":"Carolina S.","family":"Marques","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica de \u00c9vora University of \u00c9vora, Institute for Research and Advanced Training, CLAV  Rua Rom\u00e3o Ramalho 59 7000 \u00c9vora Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8248-1116","authenticated-orcid":false,"given":"Anthony J.","family":"Burke","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica de \u00c9vora University of \u00c9vora, Institute for Research and Advanced Training, CLAV  Rua Rom\u00e3o Ramalho 59 7000 \u00c9vora Portugal"},{"name":"Department of Chemistry, School of Science and Technology University of \u00c9vora, CLAV  Rua Rom\u00e3o Ramalho 59 7000 \u00c9vora Portugal"}]}],"member":"311","published-online":{"date-parts":[[2016,10,4]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)96609-8"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1590\/S0103-50532001000300002"},{"key":"e_1_2_6_4_1","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1471-4159.1988.tb01089.x"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1080\/10253890500342321"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-1700(1998100)14:4<225::AID-SMI801>3.0.CO;2-P"},{"key":"e_1_2_6_8_1","unstructured":"\u00a0"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60109a003"},{"key":"e_1_2_6_10_2","doi-asserted-by":"crossref","first-page":"229","DOI":"10.25004\/IJPSDR.2010.020402","volume":"2","author":"Bhrigu B.","year":"2010","journal-title":"Int. J. Pharm. Sci. Drug Res."},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2005.12.004"},{"key":"e_1_2_6_12_2","first-page":"27","volume":"55","author":"Pandeya S. N.","year":"2005","journal-title":"Acta Pharm."},{"key":"e_1_2_6_13_1","unstructured":"\u00a0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201501399"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2016.02.023"},{"key":"e_1_2_6_16_2","volume-title":"Catalytic Arylation Methods\u2014From the Academic Lab to Industrial","author":"Marques C. S.","year":"2015"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.201600932"},{"key":"e_1_2_6_18_1","unstructured":"For key reviews see:"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.03.136"},{"key":"e_1_2_6_20_2","volume-title":"Topics in Heterocyclic Chemistry, Vol.\u200540: Chemistry of 1,2,3-triazoles","year":"2015"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.3109\/14756360903524304"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201100432"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.canlet.2015.10.025"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.44.969"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.9.3.397"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2015.01.044"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200600392"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200600392"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0608101"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2012.04.013"},{"key":"e_1_2_6_30_1","unstructured":"\u00a0"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo802036m"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200566s"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcata.2013.03.027"},{"key":"e_1_2_6_34_1","unstructured":"\u00a0"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc01635g"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.09.135"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201200481"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b00595"},{"key":"e_1_2_6_39_1","unstructured":"\u00a0"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2011.03.015"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2015.04.062"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.04.024"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2012.06.057"},{"key":"e_1_2_6_44_1","unstructured":"\u00a0"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2009.08.059"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB02440K"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1999-3541"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo200869a"},{"key":"e_1_2_6_49_1","unstructured":"\u00a0"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0783479"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200400657"},{"key":"e_1_2_6_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200400657"},{"key":"e_1_2_6_52_1","unstructured":"\u00a0"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201000369"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.09.053"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.03.105"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2013.04.011"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ra47000h"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201200556"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200901139"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2012.05.129"},{"key":"e_1_2_6_61_1","unstructured":"\u00a0"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol062814b"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2007.05.119"},{"key":"e_1_2_6_64_1","unstructured":"For some examples see:"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs200562n"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja905432x"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol9910767"},{"key":"e_1_2_6_68_1","unstructured":"For some examples see:"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0256062"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0002184"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527630578"},{"key":"e_1_2_6_72_1","unstructured":"For some examples see:"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0207067"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0103930"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja012711i"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja060225v"},{"key":"e_1_2_6_77_1","unstructured":"\u00a0"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/om8011163"},{"key":"e_1_2_6_79_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0ob00400f"},{"key":"e_1_2_6_80_1","volume-title":"Purification of Laboratory Chemicals, 4th.\u2005ed.","author":"Amarego W. L. F.","year":"1996"},{"key":"e_1_2_6_81_1","unstructured":"\u00a0"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.09.010"},{"key":"e_1_2_6_83_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5RA05468K"}],"container-title":["ChemCatChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcctc.201600901","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcctc.201600901","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cctc.201600901","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T13:28:32Z","timestamp":1760275712000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cctc.201600901"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,10,4]]},"references-count":85,"journal-issue":{"issue":"22","published-print":{"date-parts":[[2016,11,22]]}},"alternative-id":["10.1002\/cctc.201600901"],"URL":"https:\/\/doi.org\/10.1002\/cctc.201600901","archive":["Portico"],"relation":{},"ISSN":["1867-3880","1867-3899"],"issn-type":[{"value":"1867-3880","type":"print"},{"value":"1867-3899","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,10,4]]},"assertion":[{"value":"2016-07-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2016-10-04","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}