{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,20]],"date-time":"2025-10-20T17:55:29Z","timestamp":1760982929340,"version":"3.41.0"},"reference-count":45,"publisher":"Canadian Science Publishing","issue":"1","license":[{"start":{"date-parts":[[2009,1,1]],"date-time":"2009-01-01T00:00:00Z","timestamp":1230768000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/www.nrcresearchpress.com\/page\/about\/CorporateTextAndDataMining"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Can. J. Chem."],"published-print":{"date-parts":[[2009,1,1]]},"abstract":"<jats:p> A series of ferrocenyl oxazaphospholidine phosphines that differ electronically and sterically were investigated as ligands for the Suzuki\u2013Miyaura cross-coupling reactions. One of these compounds, 1, was shown to be highly effective in the coupling reactions of bulky aryl bromides with boronic acids when combined with Pd(OAc)<jats:sub>2<\/jats:sub>, while another, 2, was capable of coupling aryl chlorides with boronic acids. However, these ligands were less effective in asymmetric induction.Key words: Suzuki\u2013Miyaura coupling, ferrocenyl phosphines, aryl bromides, aryl chlorides, palladium. <\/jats:p>","DOI":"10.1139\/v08-113","type":"journal-article","created":{"date-parts":[[2008,12,9]],"date-time":"2008-12-09T21:20:17Z","timestamp":1228857617000},"page":"171-175","source":"Crossref","is-referenced-by-count":18,"title":["Ferrocenyl phosphine\u2013oxazaphospholidine oxide ligands for the Suzuki\u2013Miyaura coupling of hindered aryl bromides and chlorides"],"prefix":"10.1139","volume":"87","author":[{"given":"Daniele","family":"Vinci","sequence":"first","affiliation":[]},{"given":"Nelson","family":"Martins","sequence":"additional","affiliation":[]},{"given":"Ourida","family":"Saidi","sequence":"additional","affiliation":[]},{"given":"John","family":"Bacsa","sequence":"additional","affiliation":[]},{"given":"Amadeu","family":"Brigas","sequence":"additional","affiliation":[]},{"given":"Jianliang","family":"Xiao","sequence":"additional","affiliation":[]}],"member":"155","reference":[{"key":"p_1\/p_1_1","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1021\/ar00078a003","volume":"15","year":"1982","journal-title":"Suzuki. Acc. Chem. Res."},{"key":"p_2\/p_2_1","doi-asserted-by":"crossref","first-page":"1749","DOI":"10.1351\/pac198557121749","volume":"57","year":"1985","journal-title":"Suzuki. Pure Appl. Chem."},{"key":"p_3\/p_3_1","doi-asserted-by":"crossref","first-page":"848","DOI":"10.5059\/yukigoseikyokaishi.46.848","volume":"46","author":"Miyaura A.","year":"1988","journal-title":"Suzuki. J. Synth. Org. Chem. Jpn."},{"key":"p_4\/p_4_1","doi-asserted-by":"crossref","first-page":"419","DOI":"10.1351\/pac199163030419","volume":"63","year":"1991","journal-title":"Suzuki. Pure Appl. Chem."},{"key":"p_5\/p_5_1","doi-asserted-by":"crossref","first-page":"1043","DOI":"10.5059\/yukigoseikyokaishi.51.1043","volume":"51","author":"Miyaura A.","year":"1993","journal-title":"Suzuki. J. Synth. Org. Chem. Jpn."},{"key":"p_6\/p_6_1","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1351\/pac199466020213","volume":"66","year":"1994","journal-title":"Suzuki. Pure Appl. Chem."},{"key":"p_7\/p_7_1","doi-asserted-by":"crossref","first-page":"2457","DOI":"10.1021\/cr00039a007","volume":"95","author":"Miyaura A.","year":"1995","journal-title":"Suzuki. Chem. Rev."},{"key":"p_8\/p_8_1","first-page":"1","volume":"270","author":"Liu J.","year":"2007","journal-title":"Chem."},{"key":"p_9\/p_9_1","doi-asserted-by":"crossref","first-page":"977","DOI":"10.1002\/anie.199009771","volume":"29","author":"Bringmann R.","year":"1990","journal-title":"Weirich. Angew. Chem. Int. Ed."},{"key":"p_10\/p_10_1","doi-asserted-by":"crossref","first-page":"2297","DOI":"10.1016\/S0040-4020(01)86953-2","volume":"50","author":"Gant A.I.","year":"1994","journal-title":"Meyers. Tetrahedron"},{"key":"p_11\/p_11_1","doi-asserted-by":"crossref","first-page":"5446","DOI":"10.1021\/ja00252a022","volume":"109","author":"Meyers J.R.","year":"1987","journal-title":"Aitken. J. Am. Chem. Soc."},{"key":"p_12\/p_12_1","unstructured":"K. Kamikawa and M. Uemera. Synlett, 938 (2000)."},{"volume":"1943","journal-title":"Hayashi. J. Chem. Soc. Chem. Commun.","author":"Uemura A.","key":"p_13\/p_13_1"},{"key":"p_14\/p_14_1","doi-asserted-by":"crossref","first-page":"2033","DOI":"10.1021\/ol010076f","volume":"3","author":"Kamikawa A.","year":"2001","journal-title":"Uemura. Org. Lett."},{"key":"p_15\/p_15_1","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1055\/s-1999-3435","volume":"4","author":"Bringmann M.","year":"1999","journal-title":"Tasler. Synthesis"},{"key":"p_16\/p_16_1","doi-asserted-by":"crossref","first-page":"615","DOI":"10.1021\/ar000106z","volume":"34","author":"Bringmann D.","year":"2001","journal-title":"Menche. Acc. Chem. Res."},{"key":"p_17\/p_17_1","doi-asserted-by":"crossref","first-page":"2584","DOI":"10.1002\/(SICI)1521-3765(19990903)5:9<2584::AID-CHEM2584>3.0.CO;2-B","volume":"5","author":"Nicolaou H.","year":"1999","journal-title":"Rubsam. Chem. Eur. J."},{"key":"p_18\/p_18_1","doi-asserted-by":"crossref","first-page":"12051","DOI":"10.1021\/ja005622z","volume":"122","author":"Yin S.L.","year":"2000","journal-title":"Buchwald. J. Am. Chem. Soc."},{"key":"p_19\/p_19_1","doi-asserted-by":"crossref","first-page":"9346","DOI":"10.1002\/chem.200600616","volume":"12","author":"Genov A.","year":"2006","journal-title":"Espinet. Chem. Eur. J."},{"key":"p_20\/p_20_1","doi-asserted-by":"crossref","first-page":"1871","DOI":"10.1002\/anie.200353615","volume":"43","author":"Walker T.E.","year":"2004","journal-title":"Buchwald. Angew. Chem. Int. Ed."},{"key":"p_21\/p_21_1","doi-asserted-by":"crossref","first-page":"1162","DOI":"10.1021\/ja017082r","volume":"124","author":"Yin M.P.","year":"2002","journal-title":"Buchwald. J. Am. Chem. Soc."},{"key":"p_22\/p_22_1","doi-asserted-by":"crossref","first-page":"2413","DOI":"10.1002\/(SICI)1521-3773(19990816)38:16<2413::AID-ANIE2413>3.0.CO;2-H","volume":"38","author":"Wolfe S.L.","year":"1999","journal-title":"Buchwald. Angew. Chem. Int. Ed."},{"key":"p_23\/p_23_1","doi-asserted-by":"crossref","first-page":"9550","DOI":"10.1021\/ja992130h","volume":"121","author":"Wolfe R.A.","year":"1999","journal-title":"Buchwald. J. Am. Chem. Soc."},{"key":"p_24\/p_24_1","doi-asserted-by":"crossref","first-page":"9722","DOI":"10.1021\/ja982250+","volume":"120","author":"Old J.P.","year":"1998","journal-title":"Buchwald. J. Am. Chem. Soc."},{"key":"p_25\/p_25_1","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.molcata.2003.08.002","volume":"209","author":"Gurbuz I.","year":"2004","journal-title":"Centinkaya. J. Mol. Catal."},{"key":"p_26\/p_26_1","doi-asserted-by":"crossref","first-page":"1345","DOI":"10.1016\/j.tet.2006.12.001","volume":"63","author":"Cho H.K.","year":"2007","journal-title":"J. Yoond. Tetrahedron"},{"key":"p_27\/p_27_1","doi-asserted-by":"crossref","first-page":"4685","DOI":"10.1021\/ja042491j","volume":"127","author":"Barder S.D.","year":"2005","journal-title":"Buchwald. J. Am. Chem. Soc."},{"key":"p_28\/p_28_1","doi-asserted-by":"crossref","first-page":"4101","DOI":"10.1021\/ja057704z","volume":"128","author":"Marion O.","year":"2006","journal-title":"Nolan. J. Am. Chem. Soc."},{"key":"p_29\/p_29_1","doi-asserted-by":"crossref","first-page":"3358","DOI":"10.1021\/ja068577p","volume":"129","author":"Billingsley S.L.","year":"2007","journal-title":"Buchwald. J. Am. Chem. Soc."},{"key":"p_30\/p_30_1","doi-asserted-by":"crossref","unstructured":"A.N. Cammidge and K.V.L. Cr\u00e9py. Chem. Commun. 1723, (2000).","DOI":"10.1039\/b004513f"},{"key":"p_31\/p_31_1","doi-asserted-by":"crossref","first-page":"4377","DOI":"10.1016\/j.tet.2003.11.095","volume":"60","author":"Cammidge K.V.L.","year":"2004","journal-title":"Tetrahedron"},{"key":"p_32\/p_32_1","doi-asserted-by":"crossref","first-page":"4897","DOI":"10.1021\/jo034298y","volume":"68","author":"Herrbach O.","year":"2003","journal-title":"J. Org. Chem."},{"key":"p_33\/p_33_1","doi-asserted-by":"crossref","first-page":"659","DOI":"10.1016\/S0957-4166(02)00169-6","volume":"13","author":"Castanet F.","year":"2002","journal-title":"Asymmetry"},{"key":"p_34\/p_34_1","doi-asserted-by":"crossref","first-page":"1991","DOI":"10.1021\/ol050471w","volume":"7","author":"Hadei E.A.B.","year":"2005","journal-title":"Organ. Org. Lett."},{"key":"p_35\/p_35_1","doi-asserted-by":"crossref","first-page":"7674","DOI":"10.1002\/anie.200602482","volume":"45","author":"Arrayas J.","year":"2006","journal-title":"Carretero. Angew. Chem. Int. Ed."},{"key":"p_36\/p_36_1","doi-asserted-by":"crossref","unstructured":"F.Y. Kwong, W.H. Lam, C.H. Yeung, K.S. Chan, and A.S.C. Chan. Chem. Commun. 1922 (2004).","DOI":"10.1039\/B407243J"},{"key":"p_37\/p_37_1","doi-asserted-by":"crossref","first-page":"2592","DOI":"10.1021\/jo0265479","volume":"68","author":"Pickett F.X.","year":"2003","journal-title":"J. Richards. J. Org. Chem."},{"key":"p_38\/p_38_1","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1021\/ol0523704","volume":"2","author":"Vinci N.","year":"2006","journal-title":"J. Xiao. Org. Lett."},{"key":"p_39\/p_39_1","unstructured":"Bruker AXS, Inc. SAINT-PLUS. Version 6.45a [computer program]. Bruker AXS Inc., Madison, Wisconsin. 2005."},{"key":"p_40\/p_40_1","unstructured":"Bruker AXS, Inc. SADABS. Version 2007-2 [computer program]. Bruker AXS Inc., Madison, Wisconsin. 2007."},{"key":"p_41\/p_41_1","unstructured":"G.M. Sheldrick. SHELXL-97 [computer program]. University of G\u00f6ttingen, Germany. 1997."},{"key":"p_42\/p_42_1","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1016\/S1472-7862(02)00030-8","volume":"1","year":"2001","journal-title":"J. Barbour. J. Supramol. Chem."},{"key":"p_43\/p_43_1","doi-asserted-by":"crossref","first-page":"5749","DOI":"10.1002\/anie.200352858","volume":"42","author":"Hills M.R.","year":"2003","journal-title":"Fu. Angew. Chem. Int. Ed."},{"key":"p_44\/p_44_1","doi-asserted-by":"crossref","first-page":"3025","DOI":"10.1021\/ol034943n","volume":"5","author":"Jensen M.","year":"2003","journal-title":"Johannsen. Org. Lett."},{"key":"p_45\/p_45_1","doi-asserted-by":"crossref","first-page":"7779","DOI":"10.1021\/jo048963u","volume":"69","author":"Baillie L.","year":"2004","journal-title":"J. Xiao. J. Org. Chem."}],"container-title":["Canadian Journal of Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/cdnsciencepub.com\/doi\/pdf\/10.1139\/v08-113","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,7,2]],"date-time":"2025-07-02T16:39:53Z","timestamp":1751474393000},"score":1,"resource":{"primary":{"URL":"https:\/\/cdnsciencepub.com\/doi\/10.1139\/v08-113"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,1,1]]},"references-count":45,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2009,1,1]]}},"alternative-id":["10.1139\/v08-113"],"URL":"https:\/\/doi.org\/10.1139\/v08-113","relation":{},"ISSN":["0008-4042","1480-3291"],"issn-type":[{"type":"print","value":"0008-4042"},{"type":"electronic","value":"1480-3291"}],"subject":[],"published":{"date-parts":[[2009,1,1]]}}}