{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T11:10:16Z","timestamp":1791457816072,"version":"4.3.4"},"reference-count":65,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2020,2,4]],"date-time":"2020-02-04T00:00:00Z","timestamp":1580774400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100009591","name":"Ministerium f\u00fcr Innovation, Wissenschaft und Forschung des Landes Nordrhein-Westfalen","doi-asserted-by":"publisher","award":["NRW R\u00fcckkehrerprogramm 2009"],"award-info":[{"award-number":["NRW R\u00fcckkehrerprogramm 2009"]}],"id":[{"id":"10.13039\/501100009591","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["Heisenberg Program"],"award-info":[{"award-number":["Heisenberg Program"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000921","name":"European Cooperation in Science and Technology","doi-asserted-by":"publisher","award":["COST Action CHAOS"],"award-info":[{"award-number":["COST Action CHAOS"]}],"id":[{"id":"10.13039\/501100000921","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001655","name":"Deutscher Akademischer Austauschdienst","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001655","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100005156","name":"Alexander von Humboldt-Stiftung","doi-asserted-by":"publisher","award":["Georg Forster Program"],"award-info":[{"award-number":["Georg Forster Program"]}],"id":[{"id":"10.13039\/100005156","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemSusChem"],"published-print":{"date-parts":[[2020,3,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Cu\/TEMPO catalyst systems are known for the selective transformation of alcohols to aldehydes, as well as for the simultaneous coupling of alcohols and amines to imines under oxidative conditions. In this study, such a Cu\/TEMPO catalyst system is found to catalyze the <jats:italic>N<\/jats:italic>\u2010formylation of a variety of amines by initial oxidative activation of methanol as the carbonyl source via formaldehyde and formation of <jats:italic>N,O<\/jats:italic>\u2010hemiacetals and oxidation of the latter under very mild conditions. A vast range of amines, including aromatic and aliphatic, primary and secondary, and linear and cyclic amines are formylated under these conditions with good to excellent yields. Moreover, paraformaldehyde can be used instead of methanol for the <jats:italic>N<\/jats:italic>\u2010formylation.<\/jats:p>","DOI":"10.1002\/cssc.201903266","type":"journal-article","created":{"date-parts":[[2020,1,9]],"date-time":"2020-01-09T04:51:40Z","timestamp":1578545500000},"page":"882-887","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":37,"title":["Copper\u2010Catalyzed Formylation of Amines by using Methanol as the C1 Source"],"prefix":"10.1002","volume":"13","author":[{"given":"Manuel Carmona","family":"Pichardo","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Cologne  Greinstr. 6 50939 K\u00f6ln Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ghazal","family":"Tavakoli","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Cologne  Greinstr. 6 50939 K\u00f6ln Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jessica E.","family":"Armstrong","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Cologne  Greinstr. 6 50939 K\u00f6ln Germany"},{"name":"Department of Chemistry Yale University  225 Prospect St New Haven CT, 06511\u20138499 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tobias","family":"Wilczek","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Cologne  Greinstr. 6 50939 K\u00f6ln Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bradley E.","family":"Thomas","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Cologne  Greinstr. 6 50939 K\u00f6ln Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2155-8006","authenticated-orcid":false,"given":"Martin H. G.","family":"Prechtl","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Cologne  Greinstr. 6 50939 K\u00f6ln Germany"},{"name":"Department of Science and Environment Roskilde University  Universitetsvej 1 4000 Roskilde Denmark"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,2,4]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.68.3573"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)00910-2"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39950001319"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1995.575"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01351a623"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2010.08.023"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1982-30034"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00196a"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00080a001"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201105516"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201105516"},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b00116"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja953097b"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/s42004-019-0109-4"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC01992C"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01538a036"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol400639m"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201700681"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201700681"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.8b04286"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200901896"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201302396"},{"key":"e_1_2_2_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2009.06.007"},{"key":"e_1_2_2_22_1","first-page":"243","volume-title":"Advances in Catalysis, Vol.\u200531","author":"Klier K.","year":"1982"},{"key":"e_1_2_2_23_1","volume-title":"Oxidation of Alcohols to Aldehydes and Ketones","author":"Tojo G.","year":"2010"},{"key":"e_1_2_2_24_1","volume-title":"Oxidation of Primary Alcohols to Carboxylic Acids","author":"Tojo G.","year":"2010"},{"key":"e_1_2_2_25_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1001"},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)75204-X"},{"key":"e_1_2_2_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00170a070"},{"key":"e_1_2_2_28_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature11891"},{"key":"e_1_2_2_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja206230h"},{"key":"e_1_2_2_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2009.11.007"},{"key":"e_1_2_2_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/b001854f"},{"key":"e_1_2_2_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900478"},{"key":"e_1_2_2_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200353458"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200353458"},{"key":"e_1_2_2_34_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.274.5295.2044"},{"key":"e_1_2_2_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201403110"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201403110"},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja5070137"},{"key":"e_1_2_2_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/recl.19660850503"},{"key":"e_1_2_2_38_1","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2012.057"},{"key":"e_1_2_2_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200901245"},{"key":"e_1_2_2_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00323a064"},{"key":"e_1_2_2_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3CC47081D"},{"key":"e_1_2_2_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309634"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309634"},{"key":"e_1_2_2_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja409241h"},{"key":"e_1_2_2_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja3117203"},{"key":"e_1_2_2_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo2020399"},{"key":"e_1_2_2_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b03931"},{"key":"e_1_2_2_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201906130"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201906130"},{"key":"e_1_2_2_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b01036"},{"key":"e_1_2_2_49_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms4621"},{"key":"e_1_2_2_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201503737"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201503737"},{"key":"e_1_2_2_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201600824"},{"key":"e_1_2_2_52_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2010.08.106"},{"key":"e_1_2_2_53_1","doi-asserted-by":"publisher","DOI":"10.3390\/catal8120671"},{"key":"e_1_2_2_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201001651"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201001651"},{"key":"e_1_2_2_55_1","doi-asserted-by":"publisher","DOI":"10.1016\/0010-8545(87)85002-6"},{"key":"e_1_2_2_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01033a004"},{"key":"e_1_2_2_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic50195a040"}],"container-title":["ChemSusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcssc.201903266","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.201903266","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cssc.201903266","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.201903266","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T07:44:46Z","timestamp":1760427886000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cssc.201903266"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,2,4]]},"references-count":65,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2020,3,9]]}},"alternative-id":["10.1002\/cssc.201903266"],"URL":"https:\/\/doi.org\/10.1002\/cssc.201903266","archive":["Portico"],"relation":{},"ISSN":["1864-5631","1864-564X"],"issn-type":[{"value":"1864-5631","type":"print"},{"value":"1864-564X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,2,4]]},"assertion":[{"value":"2019-11-27","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-02-04","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}