{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,28]],"date-time":"2026-02-28T04:38:07Z","timestamp":1772253487358,"version":"3.50.1"},"reference-count":46,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2020,12,21]],"date-time":"2020-12-21T00:00:00Z","timestamp":1608508800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["KE 756\/34-1"],"award-info":[{"award-number":["KE 756\/34-1"]}],"id":[{"id":"10.13039\/501100001659","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":[[2021,1,21]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The development of C\u2212N bond formation reactions is highly desirable due to their importance in biology and chemistry. Recent progress in 3d metal catalysis is indicative of unique selectivity patterns that may permit solving challenges of chemical synthesis. We report here on a catalytic C\u2212N bond formation reaction\u2014the reductive alkylation of nitriles. Aldehydes or ketones and nitriles, all abundantly available and low\u2010cost starting materials, undergo a reductive coupling to form secondary alkylamines and inexpensive hydrogen is used as the reducing agent. The reaction has a very broad scope and many functional groups, including hydrogenation\u2010sensitive examples, are tolerated. We developed a novel cobalt catalyst, which is nanostructured, reusable, and easy to handle. The key seems the earth\u2010abundant metal in combination with a porous support material, N\u2010doped SiC, synthesized from acrylonitrile and a commercially available polycarbosilane.<\/jats:p>","DOI":"10.1002\/chem.202004755","type":"journal-article","created":{"date-parts":[[2020,11,25]],"date-time":"2020-11-25T09:40:16Z","timestamp":1606297216000},"page":"1609-1614","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["General Synthesis of Secondary Alkylamines by Reductive Alkylation of Nitriles by Aldehydes and Ketones"],"prefix":"10.1002","volume":"27","author":[{"given":"Timon","family":"Sch\u00f6nauer","sequence":"first","affiliation":[{"name":"Inorganic Chemistry II\u2014Catalyst Design University of Bayreuth  95440 Bayreuth Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1636-0508","authenticated-orcid":false,"given":"Sabrina L. J.","family":"Thom\u00e4","sequence":"additional","affiliation":[{"name":"Mesostructured Materials Department of Chemistry University of Bayreuth  95440 Bayreuth Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Leah","family":"Kaiser","sequence":"additional","affiliation":[{"name":"Inorganic Chemistry II\u2014Catalyst Design University of Bayreuth  95440 Bayreuth Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8207-8316","authenticated-orcid":false,"given":"Mirijam","family":"Zobel","sequence":"additional","affiliation":[{"name":"Mesostructured Materials Department of Chemistry University of Bayreuth  95440 Bayreuth Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9138-4155","authenticated-orcid":false,"given":"Rhett","family":"Kempe","sequence":"additional","affiliation":[{"name":"Inorganic Chemistry II\u2014Catalyst Design University of Bayreuth  95440 Bayreuth Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,12,21]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527619191"},{"key":"e_1_2_2_2_1","volume-title":"Synthesis of Best-Seller Drugs","author":"Vardanyan R.","year":"2016"},{"key":"e_1_2_2_3_1","volume-title":"Amines: Synthesis Properties and Applications","author":"Lawrence S. A.","year":"2004"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00340"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00306"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00286C"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00248"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00667"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr300389u"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0306788"},{"key":"e_1_2_2_11_1","unstructured":"We analyzed the product scope discussed in the review articles cited. Borrowing hydrogen or hydrogen autotransfer and reductive amination is strong regarding the synthesis of aryl-alkylamines or primary amines and about 10\u2009% of the reported scope are secondary alkylamines mostly with significantly lower isolated yields. Hydroaminomethylation has been reported dominantly for the synthesis of tertiary alkylamines and rarely for that of aryl-alkylamines. The intermolecular hydroamination of alkylamines and olefins giving secondary alkylamines is challenging and much less explored in comparison to the intramolecular version and alkyne hydroaminations."},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja1080019"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103137"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103137"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-17588-5"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00334J"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201709010"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201709010"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00068"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00507"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00361"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00372"},{"key":"e_1_2_2_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00547"},{"key":"e_1_2_2_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00555"},{"key":"e_1_2_2_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00404"},{"key":"e_1_2_2_24_1","doi-asserted-by":"publisher","DOI":"10.1070\/RC1999v068n01ABEH000389"},{"key":"e_1_2_2_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b04879"},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b03439"},{"key":"e_1_2_2_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201601843"},{"key":"e_1_2_2_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b07368"},{"key":"e_1_2_2_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b02394"},{"key":"e_1_2_2_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CY01577A"},{"key":"e_1_2_2_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19420751241"},{"key":"e_1_2_2_32_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4GC00536H"},{"key":"e_1_2_2_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201402527"},{"key":"e_1_2_2_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA21415K"},{"key":"e_1_2_2_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcis.2017.04.053"},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aap8004"},{"key":"e_1_2_2_37_1","doi-asserted-by":"publisher","DOI":"10.1007\/s40843-017-9140-5"},{"key":"e_1_2_2_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7NJ02727C"},{"key":"e_1_2_2_39_1","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.1601945"},{"key":"e_1_2_2_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcat.2019.01.004"},{"key":"e_1_2_2_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC04963K"},{"key":"e_1_2_2_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcat.2019.10.011"},{"key":"e_1_2_2_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6TA09293D"},{"key":"e_1_2_2_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.202000856"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202004755","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202004755","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202004755","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:41:46Z","timestamp":1760272906000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202004755"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,12,21]]},"references-count":46,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2021,1,21]]}},"alternative-id":["10.1002\/chem.202004755"],"URL":"https:\/\/doi.org\/10.1002\/chem.202004755","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,12,21]]},"assertion":[{"value":"2020-10-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-12-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}