{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T12:11:46Z","timestamp":1791461506341,"version":"4.3.4"},"reference-count":71,"publisher":"Wiley","issue":"38","license":[{"start":{"date-parts":[[2013,8,9]],"date-time":"2013-08-09T00:00:00Z","timestamp":1376006400000},"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":[[2013,9,16]]},"DOI":"10.1002\/anie.201304188","type":"journal-article","created":{"date-parts":[[2013,8,9]],"date-time":"2013-08-09T12:39:01Z","timestamp":1376051941000},"page":"10035-10039","source":"Crossref","is-referenced-by-count":167,"title":["A General, Practical Palladium\u2010Catalyzed Cyanation of (Hetero)Aryl Chlorides and Bromides"],"prefix":"10.1002","volume":"52","author":[{"given":"Todd D.","family":"Senecal","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei","family":"Shu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen L.","family":"Buchwald","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,8,9]]},"reference":[{"key":"e_1_2_3_1_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15004a"},{"key":"e_1_2_3_2_2","unstructured":"\u00a0"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.188401702202"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60126a003"},{"key":"e_1_2_3_5_2","unstructured":"\u00a0"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19190520840"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19314880107"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00080a006"},{"key":"e_1_2_3_9_2","unstructured":"\u00a0"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200804497"},{"key":"e_1_2_3_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804497"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0299708"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1973.471"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C0MD00135J"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2042035"},{"key":"e_1_2_3_15_2","unstructured":"\u00a0"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja066931d"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja078298h"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)00384-1"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100346g"},{"key":"e_1_2_3_20_2","unstructured":"\u00a0"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/om970842f"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201000807"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol3014914"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo3025829"},{"key":"e_1_2_3_25_2","unstructured":"\u00a0"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/B400562G"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2004.08.020"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.12.087"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200800733"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0481250"},{"key":"e_1_2_3_31_2","unstructured":"\u00a0"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200800295"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.05.124"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10562-010-0385-1"},{"key":"e_1_2_3_35_2","unstructured":"\u00a0"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201005121"},{"key":"e_1_2_3_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201005121"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol1028892"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.09.088"},{"key":"e_1_2_3_39_2","unstructured":"\u00a0"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2SC20903A"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol401208t"},{"key":"e_1_2_3_42_2","unstructured":"Reactions performed with a base loading below 0.125\u2005equiv resulted in incomplete conversions. The use of excess base (>0.5\u2005equiv) is not recommended as it may lead to an increased rate of cyanide dissociation from the iron center and catalyst poisoning."},{"key":"e_1_2_3_43_2","unstructured":"Other bases examined in initial experiments: Na2CO3and K3PO4."},{"key":"e_1_2_3_44_2","unstructured":"To circumvent this issue Kwong and co\u2010workers precomplexed ligand and Pd(OAc)2in freshly distilled dichloromethane and Et3N with the aid of a heat gun see Ref.\u2005[16]."},{"key":"e_1_2_3_45_2","unstructured":"\u00a0"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103882"},{"key":"e_1_2_3_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103882"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2102373"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9637098"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/om201217r"},{"key":"e_1_2_3_50_2","unstructured":"\u00a0"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1998-1651"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1998.425"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0601038"},{"key":"e_1_2_3_54_2","first-page":"543","author":"Cheng Y.\u2010n.","year":"2007","journal-title":"Synlett"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/aoc.1639"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2010.10.002"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja300827t"},{"key":"e_1_2_3_58_2","unstructured":"For the Pd\u2010catalyzed cyanation of 4\u2010iodopyrazoles see"},{"key":"e_1_2_3_59_2","unstructured":"M. E.Fraley J. P.Peckham K. L.Arrington W. F.Hoffman G. D.Hartman(Merck & Co. Inc.) WO\u201003011837 2003;"},{"key":"e_1_2_3_60_2","unstructured":"(Aventis Pharma GMBH) EP\u20101433788 2004;"},{"key":"e_1_2_3_61_2","unstructured":"M.Sakagami H.Hashizume S.Tanaka T.Okuno H.Yari K.Tonogaki K.Kouyama(Shionogi & Co. Ltd.) WO\u20102009131096 2009."},{"key":"e_1_2_3_62_2","unstructured":"For the Pd\u2010catalyzed cyanation of 3\u2010bromoindazoles see"},{"key":"e_1_2_3_63_2","first-page":"1203","author":"Cottyn B.","year":"2007","journal-title":"Synlett"},{"key":"e_1_2_3_64_2","unstructured":"K. A.Ahrendt A. J.Buchmelter J.DeMesse J.Grina J. D.Hansen E. R.Laird P.Lunghoffer D.Moreno B.Newhouse L.Ren J.Seo H.Tian S. M.Wenglowsky B.Feng J.Guzner K.Malesky S.Mathieu J.Rudolph Z.Wen W. B.Young(Array Biopharma Inc.; Genentech Inc.) WO\u20102009111279 2009;"},{"key":"e_1_2_3_65_2","unstructured":"A. P.Degnan G. O.Tora D. J.Denhart V. M.Vrudhula J. E.Macor J. J.Bronson(Bristol\u2010Myers Squibb Company) WO\u20102009009411 2009."},{"key":"e_1_2_3_66_2","unstructured":"Cyanation of 4\u2010bromo\u2010N\u2010tritylimidazole yielded little product because of low solubility under the reaction conditons."},{"key":"e_1_2_3_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0602571"},{"key":"e_1_2_3_68_2","unstructured":"Product was isolated as a 95:5 mixture of5\/4."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201304188","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201304188","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T05:47:20Z","timestamp":1697435240000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201304188"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,8,9]]},"references-count":71,"journal-issue":{"issue":"38","published-print":{"date-parts":[[2013,9,16]]}},"alternative-id":["10.1002\/anie.201304188"],"URL":"https:\/\/doi.org\/10.1002\/anie.201304188","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,8,9]]}}}