{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,24]],"date-time":"2026-04-24T06:56:41Z","timestamp":1777013801246,"version":"3.51.4"},"reference-count":45,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2011,5,11]],"date-time":"2011-05-11T00:00:00Z","timestamp":1305072000000},"content-version":"vor","delay-in-days":2,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Adv Synth Catal"],"published-print":{"date-parts":[[2011,5,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The [2+3]\u2009cycloaddition of nitriles (RCN) with 2,2\u2010dimethyl\u20103,4\u2010dihydro\u20102<jats:italic>H<\/jats:italic>\u2010pyrrole 1\u2010oxide, in the presence of palladium dichloride (PdCl<jats:sub>2<\/jats:sub>) gives the corresponding 2,3\u2010dihydro[1.2.4]oxadiazole (\u0394<jats:sup>4<\/jats:sup>\u20101,2,4\u2010oxadiazoline) palladium(II) complexes <jats:bold>1<\/jats:bold>\u2013<jats:bold>4<\/jats:bold> in good yields. However, the Pd(II)\u2010assisted reaction of pentafluorobenzonitrile with the same pyrroline <jats:italic>N<\/jats:italic>\u2010oxide gives a mixture of oxadiazoline <jats:bold>5<\/jats:bold>, ketoimine <jats:bold>6<\/jats:bold> and pyrrolylbenzamide\u2010ketoimine <jats:bold>7<\/jats:bold> Pd(II) complexes, which affords upon heating in refluxing acetone the unprecedented fused tricyclic ketoimine complex <jats:bold>8<\/jats:bold> as the exclusive product. Under heating, compounds <jats:bold>5<\/jats:bold> and <jats:bold>7<\/jats:bold> transform to <jats:bold>6<\/jats:bold>, the latter undergoing intramolecular cyclization by nucleophilic attack of the amino moiety to the <jats:italic>ortho<\/jats:italic> carbon of the pentafluorophenyl ring leading ultimately to <jats:bold>8<\/jats:bold>. The compounds were characterized by IR, <jats:sup>1<\/jats:sup>H and <jats:sup>13<\/jats:sup>C\u2005NMR, ESI<jats:sup>+<\/jats:sup>\u2010MS, elemental analyses and, in the cases of <jats:bold>3<\/jats:bold>, <jats:bold>6<\/jats:bold>, <jats:bold>7<\/jats:bold> and <jats:bold>8<\/jats:bold>, also by X\u2010ray diffraction analyses. The catalytic properties of the Pd complexes were evaluated in Suzuki\u2013Miyaura cross\u2010coupling reactions, using supercritical carbon dioxide (scCO<jats:sub>2<\/jats:sub>) as a green solvent. Cross\u2010couplings of aryl halides with phenylboronic acid give the desired biaryl products in quantitative yields, in a short reaction time, for substrate\u2010to\u2010catalyst molar ratios as high as 4.0\u22c510<jats:sup>4<\/jats:sup>.<\/jats:p>","DOI":"10.1002\/adsc.201000909","type":"journal-article","created":{"date-parts":[[2011,5,11]],"date-time":"2011-05-11T08:56:39Z","timestamp":1305104199000},"page":"1153-1160","source":"Crossref","is-referenced-by-count":44,"title":["Oxadiazoline and Ketoimine Palladium(II) Complexes as Highly Efficient Catalysts for Suzuki\u2013Miyaura Cross\u2010Coupling Reactions in Supercritical Carbon Dioxide"],"prefix":"10.1002","volume":"353","author":[{"given":"Ricardo R.","family":"Fernandes","sequence":"first","affiliation":[]},{"given":"Jamal","family":"Lasri","sequence":"additional","affiliation":[]},{"given":"M. F\u00e1tima C. Guedes","family":"da\u2005Silva","sequence":"additional","affiliation":[]},{"given":"Ant\u00f3nio M. F.","family":"Palavra","sequence":"additional","affiliation":[]},{"given":"Jos\u00e9 A. L.","family":"da\u2005Silva","sequence":"additional","affiliation":[]},{"given":"Jo\u00e3o J. R. Fra\u00fasto","family":"da\u2005Silva","sequence":"additional","affiliation":[]},{"given":"Armando J. L.","family":"Pombeiro","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2011,5,11]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0509410"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200601663"},{"key":"e_1_2_6_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200601663"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2007.12.036"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200505473"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00039a007"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800510"},{"key":"e_1_2_6_8_2","unstructured":"\u00a0"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/b813996b"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcata.2011.02.019"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/b820680e"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.2174\/1385272053544407"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527621866"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/b803584a"},{"key":"e_1_2_6_16_2","unstructured":"\u00a0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527613687"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar010070q"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr8004058"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.supflu.2005.11.025"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr040199o"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0683820"},{"key":"e_1_2_6_23_2","unstructured":"\u00a0"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/a802235f"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)00176-8"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)00349-5"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/b106808c"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1169(01)00418-6"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/b111430a"},{"key":"e_1_2_6_30_2","unstructured":"\u00a0"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/b200677b"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/b418669a"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/op060177z"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397910600942925"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/b607118j"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/hc.20281"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/b404406c"},{"key":"e_1_2_6_38_2","unstructured":"\u00a0"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2010.11.081"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/c004250a"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1178239"},{"key":"e_1_2_6_42_2","unstructured":"Bruker APEX2 & SAINT. Bruker AXS Inc. Madison Wisconsin USA 2004."},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767307043930"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889899006020"}],"container-title":["Advanced Synthesis &amp; Catalysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fadsc.201000909","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/adsc.201000909","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,6]],"date-time":"2025-10-06T23:51:37Z","timestamp":1759794697000},"score":1,"resource":{"primary":{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/10.1002\/adsc.201000909"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,5,9]]},"references-count":45,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2011,5,9]]}},"alternative-id":["10.1002\/adsc.201000909"],"URL":"https:\/\/doi.org\/10.1002\/adsc.201000909","archive":["Portico"],"relation":{},"ISSN":["1615-4150","1615-4169"],"issn-type":[{"value":"1615-4150","type":"print"},{"value":"1615-4169","type":"electronic"}],"subject":[],"published":{"date-parts":[[2011,5,9]]}}}