{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T12:54:04Z","timestamp":1790168044372,"version":"4.1.0"},"reference-count":35,"publisher":"Wiley","issue":"25","license":[{"start":{"date-parts":[[2009,5,13]],"date-time":"2009-05-13T00:00:00Z","timestamp":1242172800000},"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":[[2009,6,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:bold>Essential oxygen<\/jats:bold>: The title transformation involves two different modes of cyanation, <jats:italic>syn<\/jats:italic> and <jats:italic>anti<\/jats:italic>\u2005cyanopalladation, as the key steps in this catalytic reaction. These processes enable successful dicyanative cyclization of diyne and enyne derivatives (see scheme).<jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/mcontent.gif\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text><\/jats:p>","DOI":"10.1002\/anie.200900030","type":"journal-article","created":{"date-parts":[[2009,5,13]],"date-time":"2009-05-13T11:17:43Z","timestamp":1242213463000},"page":"4528-4531","source":"Crossref","is-referenced-by-count":76,"title":["Palladium\u2010Catalyzed Cyanation of Carbon\uf8ffCarbon Triple Bonds Under Aerobic Conditions"],"prefix":"10.1002","volume":"48","author":[{"given":"Shigeru","family":"Arai","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takashi","family":"Sato","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuka","family":"Koike","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michino","family":"Hayashi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Atsushi","family":"Nishida","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,6,3]]},"reference":[{"key":"e_1_2_3_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja801201r"},{"key":"e_1_2_3_2_2","unstructured":"\u00a0"},{"key":"e_1_2_3_3_2","volume":"63","author":"Funabiki T.","year":"1978","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39850000004"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39850000838"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00250a023"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)78457-7"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00297a079"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(02)01855-7"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/om0600442"},{"key":"e_1_2_3_11_2","unstructured":"\u00a0"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0448723"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0623459"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja805088r"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol703018t"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00089a006"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol060733"},{"key":"e_1_2_3_18_2","unstructured":"\u00a0"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0349195"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462961"},{"key":"e_1_2_3_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462961"},{"key":"e_1_2_3_21_2","unstructured":"Nickel and platinum catalysis were ineffective. The addition of various ligands (phosphines phosphites 1 5\u2010cyclooctadiene isonitrile and pyridine derivatives) or Lewis acids (Ag salts and TMSOTf) under palladium catalysis did not improve the chemical yield or stereoselectivity in the 1 2\u2010dicyanation of terminal alkynes."},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0272944"},{"key":"e_1_2_3_23_2","unstructured":"\u00a0"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja066931d"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0514294"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19670790125"},{"key":"e_1_2_3_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196700921"},{"key":"e_1_2_3_27_2","unstructured":"For a review of palladium with an oxidant in organic synthesis see:"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300630"},{"key":"e_1_2_3_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300630"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068006f"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0569959"},{"key":"e_1_2_3_31_2","unstructured":"See the Supporting Information."},{"key":"e_1_2_3_32_2","unstructured":"Compound8\u2009awas determined to have anE\u2005configuration based on the NOE interactions between allyl and vinyl protons."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.200900030","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.200900030","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,28]],"date-time":"2023-09-28T22:02:03Z","timestamp":1695938523000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.200900030"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,6,3]]},"references-count":35,"journal-issue":{"issue":"25","published-print":{"date-parts":[[2009,6,8]]}},"alternative-id":["10.1002\/anie.200900030"],"URL":"https:\/\/doi.org\/10.1002\/anie.200900030","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,6,3]]}}}