{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,16]],"date-time":"2026-07-16T18:13:19Z","timestamp":1784225599908,"version":"3.55.0"},"reference-count":41,"publisher":"Wiley","issue":"30","license":[{"start":{"date-parts":[[2018,6,28]],"date-time":"2018-06-28T00:00:00Z","timestamp":1530144000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100010665","name":"H2020 Marie Sk\u0142odowska-Curie Actions","doi-asserted-by":"publisher","award":["675020-MSCA-ITN-2015-ETN"],"award-info":[{"award-number":["675020-MSCA-ITN-2015-ETN"]}],"id":[{"id":"10.13039\/100010665","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2018,7,20]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Alkyl amines are an important class of organic compounds in medicinal and materials chemistry. Until now very have been very few methods for the synthesis of alkyl amines by metal\u2010catalyzed cross\u2010coupling of alkyl electrophiles with nitrogen nucleophiles. Described here is an approach to employ tandem photoredox and copper catalysis to enable the cross\u2010coupling of alkyl <jats:italic>N<\/jats:italic>\u2010hydroxyphthalimide esters, readily derived from alkyl carboxylic acids, with benzophenone\u2010derived imines. Hydrolysis of the coupling products furnish alkylated primary amines. Primary, secondary, and tertiary alkyl groups can be transferred, and the coupling tolerates a diverse set of functional groups. The method allows rapid functionalization of natural products and drugs, and can be used to expedite syntheses of pharmaceuticals from readily available chemical feedstocks.<\/jats:p>","DOI":"10.1002\/anie.201804873","type":"journal-article","created":{"date-parts":[[2018,6,4]],"date-time":"2018-06-04T16:22:20Z","timestamp":1528129340000},"page":"9501-9504","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":118,"title":["Cross\u2010Coupling of Alkyl Redox\u2010Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis"],"prefix":"10.1002","volume":"57","author":[{"given":"Runze","family":"Mao","sequence":"first","affiliation":[{"name":"Laboratory of Inorganic Synthesis and Catalysis Institute of Chemical Sciences and Engineering \u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL) ISIC-LSCI  BCH 3305 1015 Lausanne Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonathan","family":"Balon","sequence":"additional","affiliation":[{"name":"Laboratory of Inorganic Synthesis and Catalysis Institute of Chemical Sciences and Engineering \u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL) ISIC-LSCI  BCH 3305 1015 Lausanne Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8335-1196","authenticated-orcid":false,"given":"Xile","family":"Hu","sequence":"additional","affiliation":[{"name":"Laboratory of Inorganic Synthesis and Catalysis Institute of Chemical Sciences and Engineering \u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne (EPFL) ISIC-LSCI  BCH 3305 1015 Lausanne Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,6,28]]},"reference":[{"key":"e_1_2_2_1_1","volume-title":"Amines: Synthesis Properties and Applications","author":"Lawrence S. A.","year":"2004"},{"key":"e_1_2_2_2_1","volume-title":"Amino Group Chemistry: From Synthesis to the Life Sciences","author":"Ricci A.","year":"2008"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00722-0"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301202"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301202"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja4126609"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aad8313"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b07546"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b10907"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b09582"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.6b00187"},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms12494"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-017-0023-z"},{"key":"e_1_2_2_13_1","unstructured":"For representative examples see:"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b00250"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaf6123"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201612314"},{"key":"e_1_2_2_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201612314"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b07172"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201605463"},{"key":"e_1_2_2_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201605463"},{"key":"e_1_2_2_19_1","unstructured":"\u00a0"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b01533"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.6b00284"},{"key":"e_1_2_2_22_1","author":"Liang Y.","year":"2018","journal-title":"ChemRxiv"},{"key":"e_1_2_2_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja973524g"},{"key":"e_1_2_2_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol1005455"},{"key":"e_1_2_2_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol2032152"},{"key":"e_1_2_2_26_1","unstructured":"For pioneering work and selected reviews of tandem photoredox and nickel catalysis in C\u2212C coupling see:"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300503r"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00018"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1253647"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1255525"},{"key":"e_1_2_2_31_1","unstructured":"For selected examples of tandem photoredox and copper catalysis see:"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b09802"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja301553c"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500074"},{"key":"e_1_2_2_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201500074"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b03888"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC06284A"},{"key":"e_1_2_2_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC06994K"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201804873","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201804873","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,9]],"date-time":"2023-09-09T13:02:33Z","timestamp":1694264553000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201804873"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,6,28]]},"references-count":41,"journal-issue":{"issue":"30","published-print":{"date-parts":[[2018,7,20]]}},"alternative-id":["10.1002\/anie.201804873"],"URL":"https:\/\/doi.org\/10.1002\/anie.201804873","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,6,28]]},"assertion":[{"value":"2018-04-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-06-28","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}