{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,14]],"date-time":"2026-09-14T17:02:47Z","timestamp":1789405367380,"version":"build-2803163510"},"reference-count":57,"publisher":"American Chemical Society (ACS)","issue":"13","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[2010,7,2]]},"DOI":"10.1021\/ol101080q","type":"journal-article","created":{"date-parts":[[2010,6,3]],"date-time":"2010-06-03T14:39:24Z","timestamp":1275575964000},"page":"3066-3069","source":"Crossref","is-referenced-by-count":104,"title":["Preparation of Tetrasubstituted Furans via Intramolecular Wittig Reactions with Phosphorus Ylides as Intermediates"],"prefix":"10.1021","volume":"12","author":[{"given":"Tzu-Ting","family":"Kao","sequence":"first","affiliation":[{"name":"Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei 11677, Taiwan, Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Siang-en","family":"Syu","sequence":"additional","affiliation":[{"name":"Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei 11677, Taiwan, Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi-Wun","family":"Jhang","sequence":"additional","affiliation":[{"name":"Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei 11677, Taiwan, Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenwei","family":"Lin","sequence":"additional","affiliation":[{"name":"Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei 11677, Taiwan, Republic of China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2010,6,3]]},"reference":[{"key":"ref1\/cit1","unstructured":"For recent reviews, see:"},{"key":"ref1\/cit1a","unstructured":"aHou, X. L., Yang, Z., and Wong, H. N. C.Progress in Heterocyclic Chemistry;Gribble, G. W. and Joule, J. A., Eds.Pergamon:Oxford, UK, 2008; Vol. 19, p176."},{"key":"ref1\/cit1b","unstructured":"bKeay, B. A. and Dibble, P. W.Comprehensive Heterocyclic Chemistry II;Katritzky, A. R., Rees, C. W., and Scriven, E. F. V., Eds.Elsevier:Oxford, UK, 1997; Vol. 2, p395."},{"key":"ref1\/cit1c","doi-asserted-by":"crossref","first-page":"1955","DOI":"10.1016\/S0040-4020(97)10303-9","volume":"54","author":"Hou X. L.","year":"1998","journal-title":"Tetrahedron"},{"key":"ref1\/cit1d","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1039\/a809439j","volume":"28","author":"Keay B. A.","year":"1999","journal-title":"Chem. Soc. Rev."},{"key":"ref1\/cit1e","first-page":"2849","author":"Gilchrist T. L.","year":"1999","journal-title":"J. Chem. Soc., Faraday Trans. 1"},{"key":"ref2\/cit2a","doi-asserted-by":"crossref","first-page":"795","DOI":"10.1021\/cr00075a005","volume":"86","author":"Lipshutz B. 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Ed."},{"key":"ref3\/cit3c","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1016\/S0022-328X(98)01051-1","volume":"576","author":"Cacchi S.","year":"1999","journal-title":"J. Organomet. Chem."},{"key":"ref4\/cit4","unstructured":"For recent examples, see:"},{"key":"ref4\/cit4a","doi-asserted-by":"crossref","first-page":"3536","DOI":"10.1039\/b907330b","author":"Melzig L.","year":"2009","journal-title":"Chem. Commun."},{"key":"ref4\/cit4b","doi-asserted-by":"crossref","first-page":"10280","DOI":"10.1002\/chem.200901432","volume":"15","author":"Sn\u00e9garoff K.","year":"2009","journal-title":"Chem.\u2014Eur. J."},{"key":"ref4\/cit4c","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1039\/B510866G","author":"Ila H.","year":"2006","journal-title":"Chem. Commun."},{"key":"ref4\/cit4d","doi-asserted-by":"crossref","DOI":"10.1002\/9783527619467","volume-title":"Handbook of functionalized organometallics","author":"Knochel P.","year":"2005"},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"5277","DOI":"10.1002\/ejoc.200500387","author":"Minetto G.","year":"2005","journal-title":"Eur. J. Org. Chem."},{"key":"ref6\/cit6","unstructured":"For selected examples, see:"},{"key":"ref6\/cit6a","doi-asserted-by":"crossref","first-page":"8045","DOI":"10.1021\/jo061153t","volume":"71","author":"Mross G.","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref6\/cit6b","doi-asserted-by":"crossref","first-page":"1537","DOI":"10.1002\/cber.19020350263","volume":"35","author":"Feist F.","year":"1902","journal-title":"Chem. Ber."},{"key":"ref6\/cit6c","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1002\/cber.19110440175","volume":"44","author":"B\u00e9nary E.","year":"1911","journal-title":"Chem. Ber."},{"key":"ref7\/cit7","unstructured":"For selected examples starting from allenyl ketones, see:"},{"key":"ref7\/cit7a","doi-asserted-by":"crossref","first-page":"5195","DOI":"10.1002\/anie.200701128","volume":"46","author":"Dudnik A. S.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref7\/cit7b","doi-asserted-by":"crossref","first-page":"1581","DOI":"10.1002\/anie.199515811","volume":"34","author":"Hashmi A. S. K.","year":"1995","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref7\/cit7c","doi-asserted-by":"crossref","first-page":"2285","DOI":"10.1002\/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO;2-F","volume":"39","author":"Hashmi A. S. K.","year":"2000","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref7\/cit7d","doi-asserted-by":"crossref","first-page":"7169","DOI":"10.1021\/jo00102a056","volume":"59","author":"Marshall J. A.","year":"1994","journal-title":"J. Org. Chem."},{"key":"ref7\/cit7e","doi-asserted-by":"crossref","first-page":"2447","DOI":"10.1002\/chem.200204664","volume":"9","author":"Ma S.","year":"2003","journal-title":"Chem.\u2014Eur. J."},{"key":"ref7\/cit7f","doi-asserted-by":"crossref","first-page":"432","DOI":"10.1002\/adsc.200303201","volume":"346","author":"Hashmi A. S. K.","year":"2004","journal-title":"Adv. Synth. Catal."},{"key":"ref7\/cit7g","doi-asserted-by":"crossref","first-page":"1769","DOI":"10.1021\/ol050372i","volume":"7","author":"Sniady A.","year":"2005","journal-title":"Org. Lett."},{"key":"ref7\/cit7h","doi-asserted-by":"crossref","first-page":"5409","DOI":"10.1021\/ol052160r","volume":"7","author":"Liu Y.","year":"2005","journal-title":"Org. Lett."},{"key":"ref7\/cit7i","doi-asserted-by":"crossref","first-page":"6704","DOI":"10.1002\/anie.200601252","volume":"45","author":"Zhang J.","year":"2006","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref7\/cit7j","doi-asserted-by":"crossref","first-page":"1905","DOI":"10.1002\/anie.200604299","volume":"46","author":"Peng L.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref7\/cit7k","doi-asserted-by":"crossref","first-page":"1681","DOI":"10.1002\/anie.200805531","volume":"48","author":"Zhang M.","year":"2009","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref8\/cit8","unstructured":"For recent selected examples of other tetrasubstituted furans with 2-(1-alkynyl)-2-alken-1-ones as substrates catalyzed by transition metal, see:"},{"key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"9303","DOI":"10.1002\/chem.200901386","volume":"15","author":"Liu R.","year":"2009","journal-title":"Chem.\u2014Eur. J."},{"key":"ref8\/cit8b","doi-asserted-by":"crossref","first-page":"617","DOI":"10.1002\/adsc.200800715","volume":"351","author":"Xiao Y.","year":"2009","journal-title":"Adv. Synth. Catal."},{"key":"ref8\/cit8c","doi-asserted-by":"crossref","first-page":"3594","DOI":"10.1039\/b905267d","author":"Xiao Y.","year":"2009","journal-title":"Chem. Commun."},{"key":"ref8\/cit8d","doi-asserted-by":"crossref","first-page":"5505","DOI":"10.1002\/anie.200901299","volume":"48","author":"Liu F.","year":"2009","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref8\/cit8e","doi-asserted-by":"crossref","first-page":"456","DOI":"10.1002\/chem.200901813","volume":"16","author":"Gao J.","year":"2010","journal-title":"Chem.\u2014Eur. J."},{"key":"ref8\/cit8f","doi-asserted-by":"crossref","first-page":"5208","DOI":"10.1002\/chem.200900413","volume":"15","author":"Zhang Y.","year":"2009","journal-title":"Chem.\u2014Eur. J."},{"key":"ref9\/cit9","unstructured":"For the only example of tetrasubstituted furans bearing three phenyl groups and a ketone function with poor yield, see:"},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"3421","DOI":"10.1021\/jo01263a045","volume":"34","author":"Trisler J. C.","year":"1969","journal-title":"J. Org. Chem."},{"key":"ref9\/cit9b","first-page":"1209","author":"Tseng J.-C.","year":"2006","journal-title":"Synlett."},{"key":"ref10\/cit10","unstructured":"To the best of our knowledge, there is no report with phosphorous ylides for the syntheses of furans."},{"key":"ref11\/cit11","unstructured":"For interesting phosphine-mediated reductive cyclizations of \u03b3-acyloxy butynoates to furans, see:"},{"key":"ref11\/cit11a","doi-asserted-by":"crossref","first-page":"4118","DOI":"10.1021\/ja049377l","volume":"126","author":"Jung C.-K.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref12\/cit12","unstructured":"In our one-step protocol, the addition sequence of reactants has no influence on the results of the formation of furans."},{"key":"ref13\/cit13","unstructured":"For selected reviews of Wittig reactions, see:"},{"key":"ref13\/cit13a","doi-asserted-by":"crossref","first-page":"1411","DOI":"10.1002\/1521-3773(20010417)40:8<1411::AID-ANIE1411>3.0.CO;2-U","volume":"40","author":"Hoffmann R. W.","year":"2001","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref13\/cit13b","volume-title":"Preparation of Alkenes: a Practical Approach","author":"Lawrence N. J.","year":"1995"},{"key":"ref13\/cit13c","doi-asserted-by":"crossref","DOI":"10.1002\/9783527613908","volume-title":"Phosphorus Ylides: Chemistry and Applications in Organic Chemistry","author":"Kolodiazhnyi O. I.","year":"1999"},{"key":"ref14\/cit14","unstructured":"For another method to prepare the phosphonium enolate zwitterions of type9starting from tertiary phosphines, 4-pyridinecarboxaldehyde (3 equiv), and alkynoates (1 equiv) within 0.5\u221212 h, please see:"},{"key":"ref14\/cit14a","doi-asserted-by":"crossref","first-page":"6722","DOI":"10.1021\/ja071990s","volume":"129","author":"Zhu X.-F.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref15\/cit15","unstructured":"The structures of adducts8k,9a,10f, and17were confirmed by1H,13C, and31P NMR and X-ray analyses (CCDC no. 769222 for8k, 771901 for9a, 768638 for10f, and 746224 for17)."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol101080q","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,15]],"date-time":"2023-03-15T11:21:16Z","timestamp":1678879276000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol101080q"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,6,3]]},"references-count":57,"journal-issue":{"issue":"13","published-print":{"date-parts":[[2010,7,2]]}},"alternative-id":["10.1021\/ol101080q"],"URL":"https:\/\/doi.org\/10.1021\/ol101080q","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2010,6,3]]}}}