{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T01:42:23Z","timestamp":1790646143779,"version":"4.1.0"},"reference-count":102,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2013,11,29]],"date-time":"2013-11-29T00:00:00Z","timestamp":1385683200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2014,1,7]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Primary and secondary amines can be rapidly and quantitatively oxidized to the corresponding imines by singlet oxygen. This reactive form of oxygen was produced using a variable\u2010temperature continuous\u2010flow LED\u2010photoreactor with a catalytic amount of tetraphenylporphyrin as the sensitizer. \u03b1\u2010Aminonitriles were obtained in good to excellent yields when trimethylsilyl cyanide served as an in\u2005situ imine trap. At 25\u00b0C, primary amines were found to undergo oxidative coupling prior to cyanide addition and yielded secondary \u03b1\u2010aminonitriles. Primary \u03b1\u2010aminonitriles were synthesized from the corresponding primary amines for the first time, by an oxidative Strecker reaction at \u201350 \u00b0C. This atom\u2010economic and protecting\u2010group\u2010free pathway provides a route to racemic amino acids, which was exemplified by the synthesis of\n                    <jats:italic>tert<\/jats:italic>\n                    \u2010leucine hydrochloride from neopentylamine.\n                  <\/jats:p>","DOI":"10.1002\/anie.201307778","type":"journal-article","created":{"date-parts":[[2013,11,29]],"date-time":"2013-11-29T04:29:16Z","timestamp":1385699356000},"page":"557-561","source":"Crossref","is-referenced-by-count":158,"title":["Continuous\u2010Flow Oxidative Cyanation of Primary and Secondary Amines Using Singlet Oxygen"],"prefix":"10.1002","volume":"53","author":[{"given":"Dmitry B.","family":"Ushakov","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kerry","family":"Gilmore","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel","family":"Kopetzki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"D. Tyler","family":"McQuade","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter H.","family":"Seeberger","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,11,29]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19951072205"},{"key":"e_1_2_2_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199524431"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200401082"},{"key":"e_1_2_2_4_2","unstructured":"\u00a0"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200352076"},{"key":"e_1_2_2_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352076"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0400382"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)86085-3"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2001.390"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.04.018"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4051235"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201300012"},{"key":"e_1_2_2_12_2","unstructured":"For recent examples of the aerobic oxidation of amines to imines see:"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol302584y"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc41407h"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.03.098"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201200587"},{"key":"e_1_2_2_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201200587"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3gc41186a"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201102779"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol302708r"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob06670j"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301095j"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja306934b"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304654"},{"key":"e_1_2_2_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304654"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol202857t"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc36995h"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs300604k"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2009.04.015"},{"key":"e_1_2_2_28_2","unstructured":"see Ref. [1b]."},{"key":"e_1_2_2_29_2","unstructured":"For examples of continuous\u2010flow oxidations see:"},{"key":"e_1_2_2_30_2","first-page":"869","author":"Lange H.","year":"2011","journal-title":"Synlett"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol3005529"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2017643"},{"key":"e_1_2_2_33_2","unstructured":"For reviews see:"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr010371d"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0680336"},{"key":"e_1_2_2_36_2","unstructured":"\u00a0"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(96)01858-8"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol047876l"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo701641b"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol9018166"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201108080"},{"key":"e_1_2_2_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201108080"},{"key":"e_1_2_2_42_2","unstructured":"For photoreactions in flow see:"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1556\/jfchem.2011.00007"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.12.063"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300503r"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.8.229"},{"key":"e_1_2_2_47_2","unstructured":"\u00a0"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201204558"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201107446"},{"key":"e_1_2_2_49_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107446"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1039\/a908290e"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm100762r"},{"key":"e_1_2_2_52_2","unstructured":"\u00a0"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm030091l"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1463-1326.2005.00539.x"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.2337\/diacare.27.12.2874"},{"key":"e_1_2_2_56_2","unstructured":"For the oxidative cyanation of amines see:"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)98440-5"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3010495"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200906655"},{"key":"e_1_2_2_59_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200906655"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol202659e"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja8017362"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201200961"},{"key":"e_1_2_2_62_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201200961"},{"key":"e_1_2_2_63_2","unstructured":"For a review on the photoredox functionalization of nitrogen\u2010containing compounds see:"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35203f"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201200223"},{"key":"e_1_2_2_65_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201200223"},{"key":"e_1_2_2_66_2","unstructured":"For examples of the Strecker reaction in flow see:"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201100370"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.10.087"},{"key":"e_1_2_2_69_2","first-page":"5597","author":"Wilwa C.","year":"2008","journal-title":"Eur. J. Org. Chem."},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201201539"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja045402b"},{"key":"e_1_2_2_72_2","unstructured":"For NMR data of the trimer see Ref.\u2005[23d h]."},{"key":"e_1_2_2_73_2","unstructured":"Several approaches to 1\u2010pyrroline from pyrrolidine have been described; by catalytic dehydrogenation:"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01556a023"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcat.2004.11.034"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1023\/B:RUJO.0000045903.18108.84"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19820003031"},{"key":"e_1_2_2_78_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)86146-9"},{"key":"e_1_2_2_79_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1976-24185"},{"key":"e_1_2_2_80_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19871201209"},{"key":"e_1_2_2_81_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)88474-9"},{"key":"e_1_2_2_82_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1997.311"},{"key":"e_1_2_2_83_2","unstructured":"It was found that cyanide addition to imines proceeded very slowly in highly diluted solutions (Table\u20052 entry\u20052). Therefore yields of nitriles and imines are given as a sum in Table\u20052. With more concentrated solutions only traces of imines were observed. Corresponding peaks in the1H\u2005NMR spectrum completely disappeared after concentration in\u2005vacuo."},{"key":"e_1_2_2_84_2","unstructured":"We recently reported that the outcome of the photooxidation strongly depends on the reaction temperature; for an example see Ref.\u2005[13a]."},{"key":"e_1_2_2_85_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob26733k"},{"key":"e_1_2_2_86_2","unstructured":"Contains 5\u2009% water. Other TBAF loadings (100 50 1\u2005mol\u2009%) as well as other activators such as hexamethylphosphoric triamide (HMPA) Et3N 1 4\u2010diazabicyclo[2.2.2]octane (DABCO) andN\u2010methylmorpholine\u2010N\u2010oxide (NMO) were studied; however their application was not successful."},{"key":"e_1_2_2_87_2","unstructured":"A greater amount of the dimeric products was also observed in the batch process."},{"key":"e_1_2_2_88_2","unstructured":"\u00a0"},{"key":"e_1_2_2_89_2","doi-asserted-by":"publisher","DOI":"10.1016\/0957-4166(95)00377-0"},{"key":"e_1_2_2_90_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1177(98)00009-5"},{"key":"e_1_2_2_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar700155p"},{"key":"e_1_2_2_92_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1962206"},{"key":"e_1_2_2_93_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.216"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201307778","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201307778","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T21:06:23Z","timestamp":1697490383000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201307778"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,11,29]]},"references-count":102,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2014,1,7]]}},"alternative-id":["10.1002\/anie.201307778"],"URL":"https:\/\/doi.org\/10.1002\/anie.201307778","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,11,29]]}}}