{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,23]],"date-time":"2026-04-23T17:34:43Z","timestamp":1776965683366,"version":"3.51.4"},"reference-count":59,"publisher":"Wiley","issue":"71","license":[{"start":{"date-parts":[[2018,11,26]],"date-time":"2018-11-26T00:00:00Z","timestamp":1543190400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100007136","name":"Secretar\u00eda de Estado de Investigaci\u00f3n, Desarrollo e Innovaci\u00f3n","doi-asserted-by":"publisher","award":["CTQ2017-88171-P"],"award-info":[{"award-number":["CTQ2017-88171-P"]}],"id":[{"id":"10.13039\/501100007136","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003359","name":"Generalitat Valenciana","doi-asserted-by":"publisher","award":["AICO\/2017\/007"],"award-info":[{"award-number":["AICO\/2017\/007"]}],"id":[{"id":"10.13039\/501100003359","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009092","name":"Universidad de Alicante","doi-asserted-by":"publisher","award":["UAFPU2016-034"],"award-info":[{"award-number":["UAFPU2016-034"]}],"id":[{"id":"10.13039\/100009092","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2018,12,17]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Lately, the cross\u2010dehydrogenative coupling of tetrahydroisoquinolines and nitroalkanes has become a widely studied reaction in organic chemistry; the corresponding \u03b2\u2010nitroamines are generally formed irrespective of the catalysis and activation mode utilized. A quite distinct behavior was observed when the reaction was catalyzed by copper nanoparticles supported on titania, leading to the formation of 5,6\u2010dihydroindolo[2,1\u2010<jats:italic>a<\/jats:italic>]isoquinolines with high selectivity and good yields. A meticulous reaction mechanism is proposed, based on experimentation, and discussed along with a key chemical modification of these compounds. Apparently, the catalyst effectiveness resides in its nanostructured character, outperforming the activity of the commercial copper catalysts.<\/jats:p>","DOI":"10.1002\/chem.201805137","type":"journal-article","created":{"date-parts":[[2018,10,16]],"date-time":"2018-10-16T05:06:28Z","timestamp":1539666388000},"page":"18857-18862","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Synthesis of Dihydroindoloisoquinolines through Copper\u2010Catalyzed Cross\u2010Dehydrogenative Coupling of Tetrahydroisoquinolines and Nitroalkanes"],"prefix":"10.1002","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8020-3286","authenticated-orcid":false,"given":"Iris","family":"Mart\u00edn\u2010Garc\u00eda","sequence":"first","affiliation":[{"name":"Instituto de S\u00edntesis Org\u00e1nica (ISO) and Departamento de Qu\u00edmica Org\u00e1nica Facultad de Ciencias Universidad de Alicante  Apdo. 99 03080 Alicante Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6680-3856","authenticated-orcid":false,"given":"Francisco","family":"Alonso","sequence":"additional","affiliation":[{"name":"Instituto de S\u00edntesis Org\u00e1nica (ISO) and Departamento de Qu\u00edmica Org\u00e1nica Facultad de Ciencias Universidad de Alicante  Apdo. 99 03080 Alicante Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,11,26]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-018-0021-z"},{"key":"e_1_2_2_2_1","unstructured":"\u00a0"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00097a011"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm970177c"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm980684"},{"key":"e_1_2_2_6_1","unstructured":"\u00a0"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol402908m"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol4008469"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB01239F"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC02027E"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2014.12.002"},{"key":"e_1_2_2_12_1","unstructured":"Reviews:"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300272t"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304268"},{"key":"e_1_2_2_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304268"},{"key":"e_1_2_2_15_1","unstructured":"\u00a0"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja050058j"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/b707745a"},{"key":"e_1_2_2_18_1","unstructured":"For leading and selected references see:"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.12.101"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.catcom.2009.09.017"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo901583r"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201000240"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja909145y"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0ob00261e"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja109166b"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107605"},{"key":"e_1_2_2_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201107605"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201103242"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja402479r"},{"key":"e_1_2_2_29_1","unstructured":"To the best of our knowledge (SciFinder) there are about 100 published articles reporting this transformation; approximately 650 reactions with all type of nitroalkanes and around 200 reactions involving nitroalkanes other than nitromethane."},{"key":"e_1_2_2_30_1","unstructured":"See for instance the following recent reports:"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC06869F"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201303615"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201405356"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC03421C"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.5b02626"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CY02567F"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201601702"},{"key":"e_1_2_2_38_1","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","first-page":"51","volume":"48","author":"Eastman H. E.","year":"2015","journal-title":"Aldrichimica Acta"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC01008J"},{"key":"e_1_2_2_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201500612"},{"key":"e_1_2_2_42_1","unstructured":"Reviews:"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900426"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc34659a"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300286"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.2174\/2213346101666141202234329"},{"key":"e_1_2_2_47_1","unstructured":"\u00a0"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201500787"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CY01343D"},{"key":"e_1_2_2_50_1","unstructured":"\u00a0"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300527g"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00482"},{"key":"e_1_2_2_53_1","unstructured":"The leaching assessed for the reaction of2\u2009aand3\u2009a(6\u2005wt\u2009%) was found to be rather catalytically inactive. The conversion noted in a first run after 5\u2005h was 30\u2009%. The catalyst was then removed by hot filtration after this 5\u2005h period and the filtrate heated for a further 10\u2005h giving a conversion of 40\u2009% after this total 15\u2005h period."},{"key":"e_1_2_2_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201402038"},{"key":"e_1_2_2_55_1","unstructured":"The reaction of tetrahydroisoquinoline2\u2009awith nitromethane led to the typical CDC product that is 1-(nitromethyl)-2-phenyl-1 2 3 4-tetrahydroisoquinoline."},{"key":"e_1_2_2_56_1","unstructured":"The presence of nitrites or nitrates in the reaction crude can be ruled out because of their negligible detected levels by ionic chromatography (20 and 55\u2005ng respectively in a 0.3\u2005mmol scale reaction)."},{"key":"e_1_2_2_57_1","unstructured":"Other oxidants were found to be less effective: Mn3O4 I2 CuBr\u22c5SMe2\/DABCO\/O2 DDQ CuCl\/TEMPO {DABCO=1 4-diazabicyclo[2.2.2]octane; DDQ=2 3-dichloro-5 6-dicyano-1 4-benzoquinone; TEMPO=2 2 6 6-tetramethylpiperidineN-oxide}. A thorough optimization of the amount of MnO2has not been conducted but an acceptable 80\u2009% conversion into6\u2009aahas been obtained with 10\u2005mol\u2009% MnO2after 1.5\u2005h."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201805137","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201805137","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.201805137","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201805137","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T22:10:43Z","timestamp":1760307043000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201805137"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,11,26]]},"references-count":59,"journal-issue":{"issue":"71","published-print":{"date-parts":[[2018,12,17]]}},"alternative-id":["10.1002\/chem.201805137"],"URL":"https:\/\/doi.org\/10.1002\/chem.201805137","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,11,26]]},"assertion":[{"value":"2018-10-11","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-11-26","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}