{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,21]],"date-time":"2026-04-21T10:30:56Z","timestamp":1776767456139,"version":"3.51.2"},"reference-count":64,"publisher":"Wiley","issue":"43","license":[{"start":{"date-parts":[[2013,10,2]],"date-time":"2013-10-02T00:00:00Z","timestamp":1380672000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2013,10,18]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The novel atropisomeric pyridine derivative <jats:italic>rac<\/jats:italic>\u2010<jats:bold>10<\/jats:bold> has been synthesized and structurally characterized. In contrast to its phosphorus analogue <jats:bold>3<\/jats:bold>, axially chiral <jats:bold>10<\/jats:bold> has a considerably lower rotational barrier as estimated by DFT calculations. However, the presence of the two enantiomers could be confirmed by means of chiral analytical HPLC analysis and by protonation experiments with a chiral acid. Compound <jats:italic>rac<\/jats:italic>\u2010<jats:bold>10<\/jats:bold> could be further dehydrogenated by treatment with DDQ to the benzo(<jats:italic>h<\/jats:italic>)quinoline derivative <jats:italic>rac<\/jats:italic>\u2010<jats:bold>12<\/jats:bold>. This conversion failed for the phosphorus analogue <jats:italic>rac<\/jats:italic>\u2010<jats:bold>3<\/jats:bold>. Interestingly, although 2,4,6\u2010triarylphosphinines undergo facile C\uf8ffH activation with [Cp*IrCl<jats:sub>2<\/jats:sub>]<jats:sub>2<\/jats:sub> in the presence of NaOAc, this reaction does not proceed with the corresponding pyridine derivatives. On the other hand, the latter ones can be selectively <jats:italic>ortho<\/jats:italic>\u2010metalated with Pd(OAc)<jats:sub>2<\/jats:sub>, leading to acetate\u2010bridged dimeric species, which could be unambiguously confirmed by means of X\u2010ray crystal structure analysis. The treatment of phosphinines with Pd(OAc)<jats:sub>2<\/jats:sub> led instead to the formation of the unusual cofacial oxidative coupling products <jats:bold>16<\/jats:bold> and <jats:bold>17<\/jats:bold>, which consist of a phosphorus\u2010containing cage structure.<\/jats:p>","DOI":"10.1002\/chem.201302441","type":"journal-article","created":{"date-parts":[[2013,10,11]],"date-time":"2013-10-11T21:48:40Z","timestamp":1381528120000},"page":"14458-14469","source":"Crossref","is-referenced-by-count":16,"title":["2,4,6\u2010Triarylphosphinines versus 2,4,6\u2010Triarylpyridines: An Investigation of the Differences in Reactivity between Structurally Related Aromatic Phosphorus and Nitrogen Heterocycles"],"prefix":"10.1002","volume":"19","author":[{"given":"Jarno J. M.","family":"Weemers","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jelena","family":"Wiecko","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Evgeny A.","family":"Pidko","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Manuela","family":"Weber","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Martin","family":"Lutz","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christian","family":"M\u00fcller","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2013,10,2]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19660781817"},{"key":"e_1_2_6_1_3","first-page":"846","volume":"5","year":"1966","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00742a038"},{"key":"e_1_2_6_3_2","unstructured":"\u00a0"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.01.049"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10870-006-9147-8"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200601650"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/b715197g"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800175"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/om7003546"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200801337"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.crci.2010.03.009"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0nj00030b"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201203621"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300557"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/C0CC04660D"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201200912"},{"key":"e_1_2_6_18_2","unstructured":"\u00a0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19800001895"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00332a013"},{"key":"e_1_2_6_21_2","unstructured":"DFT calculations were performed at the B3LYP\/6\u201331G level of theory using the Gaussian\u200909 program (see ref.\u2005[10]). The barrier of rotation was estimated by scanning the potential energy surface along the coordinate corresponding to the internal rotation about the Caryl\uf8ffCaryl\u2019bond with a step size of 20\u00b0."},{"key":"e_1_2_6_22_2","unstructured":"Gaussian\u200909 Revision\u2009A.01 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone B. Mennucci G.\u2005A. Petersson H. Nakatsuji M. Caricato X. Li H.\u2005P. Hratchian A.\u2005F. Izmaylov J. Bloino G. Zheng J.\u2005L. Sonnenberg M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven J.\u2005A. Montgomery \u2005Jr. J.\u2005E. Peralta F. Ogliaro M. Bearpark J.\u2005J. Heyd E. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov R. Kobayashi J. Normand K. Raghavachari A. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi N. Rega J.\u2005M. Millam M. Klene J.\u2005E. Knox J.\u2005B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. Austin R. Cammi C. Pomelli J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma V.\u2005G. Zakrzewski G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg S. Dapprich A.\u2005D. Daniels O. Farkas J.\u2005B. Foresman J.\u2005V. Ortiz J. Cioslowski and D.\u2005J. Fox Gaussian Inc. Wallingford CT 2009."},{"key":"e_1_2_6_23_2","unstructured":"\u00a0"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/b101454o"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2005.04.032"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/b712456m"},{"key":"e_1_2_6_27_2","volume-title":"Phosphorus Chemistry: Catalysis and Material Science Applications, Vol.\u200536","author":"M\u00fcller C."},{"key":"e_1_2_6_28_2","unstructured":"\u00a0"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108270194002441"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1107\/S1600536807064380"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19850001675"},{"key":"e_1_2_6_32_2","unstructured":"The four independent molecules differ in the orientation of the phenyl group in 4\u2010position of the heterocycle as well as in the orientation of the methyl\u2010napthyl\u2010group with respect to the 6\u2010membered nitrogen ring."},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/B303737A"},{"key":"e_1_2_6_34_2","unstructured":"\u00a0"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/om800909w"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/om070170l"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja060173"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/om060863m"},{"key":"e_1_2_6_39_2","unstructured":"\u00a0"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/dt9860002205"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja031543m"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0541940"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1036644"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja107780w"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2005.11.066"},{"key":"e_1_2_6_46_2","unstructured":"\u00a0"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/c29700000912"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)92682-2"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)98655-8"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)98513-9"},{"key":"e_1_2_6_51_2","first-page":"91","volume":"3","author":"Churchill M. R.","year":"1970","journal-title":"Perspect. Struct. Chem."},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.19970030422"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3765(19990702)5:7<2101::AID-CHEM2101>3.0.CO;2-0"},{"key":"e_1_2_6_54_2","volume-title":"Phosphorus Ligand Effects in Homogeneous Catalysis: Design and Synthesis","author":"M\u00fcller C.","year":"2012"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1039\/b308892h"},{"key":"e_1_2_6_56_2","unstructured":"Bruker. SAINT\u2010plus Bruker AXS Inc. Madison Wisconsin 2001."},{"key":"e_1_2_6_57_2","unstructured":"G.\u2005M. Sheldrick SADABS: Area\u2010Detector Absorption Correction University of G\u00f6ttingen G\u00f6ttingen 1999."},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767307043930"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1107\/S090744490804362X"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889809043234"},{"key":"e_1_2_6_61_2","first-page":"255","volume-title":"Crystallographic Computing","author":"Coppens P.","year":"1979"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767389011189"},{"key":"e_1_2_6_63_2","unstructured":"G.\u2005M. Sheldrick SHELXTL University of G\u00f6ttingen G\u00f6ttingen 2012."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201302441","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201302441","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T20:42:54Z","timestamp":1760301774000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201302441"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,10,2]]},"references-count":64,"journal-issue":{"issue":"43","published-print":{"date-parts":[[2013,10,18]]}},"alternative-id":["10.1002\/chem.201302441"],"URL":"https:\/\/doi.org\/10.1002\/chem.201302441","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,10,2]]}}}