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R.","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref2\/cit2e","doi-asserted-by":"crossref","first-page":"6681","DOI":"10.1016\/j.tet.2005.12.078","volume":"62","author":"McAllister G. D.","year":"2006","journal-title":"Tetrahedron"},{"key":"ref2\/cit2f","doi-asserted-by":"crossref","first-page":"6004","DOI":"10.1016\/j.tet.2007.02.056","volume":"63","author":"Bromley W. J.","year":"2007","journal-title":"Tetrahedron"},{"key":"ref3\/cit3","unstructured":"For reviews on isocyanide-based multicomponent reactions, see:"},{"key":"ref3\/cit3a","doi-asserted-by":"crossref","first-page":"1471","DOI":"10.1055\/s-2003-40507","author":"Orru R. V. A.","year":"2003","journal-title":"Synthesis"},{"key":"ref3\/cit3b","doi-asserted-by":"crossref","first-page":"899","DOI":"10.1021\/ar020258p","volume":"36","author":"Nair V.","year":"2003","journal-title":"Acc. Chem. Res."},{"key":"ref3\/cit3c","first-page":"3","volume":"113","author":"Zhu J.","year":"2003","journal-title":"Eur. J. Org. Chem."},{"key":"ref3\/cit3d","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1021\/cr0505728","volume":"106","author":"D\u00f6mling A.","year":"2006","journal-title":"Chem. Rev."},{"key":"ref3\/cit3e","doi-asserted-by":"crossref","first-page":"8444","DOI":"10.1002\/chem.200800473","volume":"14","author":"Isambert N.","year":"2008","journal-title":"Chem.\u2014Eur. J."},{"key":"ref3\/cit3f","doi-asserted-by":"crossref","first-page":"2153","DOI":"10.1016\/j.tet.2008.12.002","volume":"65","author":"El Kaim L.","year":"2009","journal-title":"Tetrahedron"},{"key":"ref3\/cit3g","doi-asserted-by":"crossref","first-page":"796","DOI":"10.1021\/cr8003407","volume":"109","author":"Wessjohann L. A.","year":"2009","journal-title":"Chem. Rev."},{"key":"ref3\/cit3h","doi-asserted-by":"crossref","DOI":"10.1002\/3527605118","volume-title":"Multicomponent Reactions","author":"Zhu J.","year":"2005"},{"key":"ref4\/cit4a","first-page":"126","volume":"51","author":"Passerini M.","year":"1921","journal-title":"Gazz. Chim. Ital."},{"key":"ref4\/cit4b","first-page":"432","volume":"52","author":"Passerini M.","year":"1922","journal-title":"Gazz. Chim. Ital."},{"key":"ref4\/cit4c","doi-asserted-by":"crossref","unstructured":"cBanfi, L.; Riva, R.InOrganic Reactions;Charette, A. B., Ed.Wiley:New York, 2005; Vol.65, pp1\u2212140.","DOI":"10.1002\/0471264180.or065.01"},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"3495","DOI":"10.1002\/anie.200600588","volume":"45","author":"Ngouansavanh T.","year":"2006","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref6\/cit6","unstructured":"MCRs involving oxidation of amines:"},{"key":"ref6\/cit6a","doi-asserted-by":"crossref","first-page":"5775","DOI":"10.1002\/anie.200701603","volume":"46","author":"Ngouansavanh T.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref6\/cit6b","doi-asserted-by":"crossref","first-page":"1509","DOI":"10.1021\/ol800199b","volume":"10","author":"Fontaine P.","year":"2008","journal-title":"Org. Lett."},{"key":"ref6\/cit6c","doi-asserted-by":"crossref","first-page":"4568","DOI":"10.1021\/ol9018166","volume":"11","author":"Jiang G.","year":"2009","journal-title":"Org. Lett."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"1762","DOI":"10.1021\/jo7022125","volume":"73","author":"Leon F.","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref8\/cit8","unstructured":"For reviews on catalytic aerobic alcohol oxidations, see:"},{"key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"3037","DOI":"10.1021\/cr0200116","volume":"104","author":"Mallat T.","year":"2004","journal-title":"Chem. Rev."},{"key":"ref8\/cit8b","doi-asserted-by":"crossref","first-page":"437","DOI":"10.1002\/9783527619405.ch5m","volume-title":"Transition Metals for Organic Synthesis","volume":"2","author":"Mark\u00f3 I. E.","year":"2004"},{"key":"ref8\/cit8e","doi-asserted-by":"crossref","first-page":"2917","DOI":"10.1016\/j.tet.2004.01.043","volume":"60","author":"Zhan B.-Z.","year":"2004","journal-title":"Tetrahedron"},{"key":"ref8\/cit8f","doi-asserted-by":"crossref","first-page":"1051","DOI":"10.1002\/adsc.200404110","volume":"346","author":"Sheldon R. A.","year":"2004","journal-title":"Adv. Synth. 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Rev."},{"key":"ref9\/cit9","unstructured":"For transition metal\/TEMPO-catalyzed aerobic alcohol oxidations, see:"},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1002\/adsc.200700282","volume":"350","author":"Gassama A.","year":"2008","journal-title":"Adv. Synth. Catal."},{"key":"ref9\/cit9b","doi-asserted-by":"crossref","first-page":"823","DOI":"10.1002\/cssc.200800144","volume":"1","author":"Jiang N.","year":"2008","journal-title":"ChemSusChem"},{"key":"ref9\/cit9c","doi-asserted-by":"crossref","first-page":"2253","DOI":"10.1002\/adsc.200700213","volume":"349","author":"Mannam S.","year":"2007","journal-title":"Adv. Synth. Cata."},{"key":"ref9\/cit9d","doi-asserted-by":"crossref","first-page":"8412","DOI":"10.1021\/ja0620336","volume":"128","author":"Shibuya M.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref9\/cit9e","doi-asserted-by":"crossref","first-page":"7087","DOI":"10.1021\/jo060837y","volume":"71","author":"Jiang N.","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref9\/cit9f","doi-asserted-by":"crossref","first-page":"923","DOI":"10.1016\/j.tetlet.2005.11.149","volume":"47","author":"Valusamy S.","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref9\/cit9g","doi-asserted-by":"crossref","first-page":"3689","DOI":"10.1021\/ol051293+","volume":"7","author":"Jiang N.","year":"2005","journal-title":"Org. Lett."},{"key":"ref9\/cit9h","first-page":"9","volume":"10","author":"Minisci F.","year":"2004","journal-title":"Eur. J. Org. Chem."},{"key":"ref9\/cit9i","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/S1381-1169(03)00286-3","volume":"204","author":"Minisci F.","year":"2003","journal-title":"J. Mol. Catal. A: Chem."},{"key":"ref9\/cit9j","doi-asserted-by":"crossref","first-page":"2414","DOI":"10.1039\/b308668b","author":"Gamez P.","year":"2003","journal-title":"Chem. Commun."},{"key":"ref9\/cit9k","doi-asserted-by":"crossref","first-page":"1507","DOI":"10.1021\/ol025721c","volume":"4","author":"Ansari I. A.","year":"2002","journal-title":"Org. Lett."},{"key":"ref9\/cit9l","doi-asserted-by":"crossref","first-page":"8650","DOI":"10.1021\/jo0105843","volume":"66","author":"Ben-Daniel R.","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref9\/cit9m","doi-asserted-by":"crossref","first-page":"6826","DOI":"10.1021\/ja0103804","volume":"123","author":"Dijksman A.","year":"2001","journal-title":"J. Am. Chem. 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J."},{"key":"ref12\/cit12","unstructured":"Mark\u00f3\u2019s procedure is an exception; see:"},{"key":"ref12\/cit12a","doi-asserted-by":"crossref","first-page":"1588","DOI":"10.1002\/anie.200353458","volume":"43","author":"Mark\u00f3 I. E.","year":"2004","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"12661","DOI":"10.1021\/ja973227b","volume":"119","author":"Mark\u00f3 I. E.","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref14\/cit14a","doi-asserted-by":"crossref","first-page":"2044","DOI":"10.1126\/science.274.5295.2044","volume":"274","author":"Mark\u00f3 I. E.","year":"1996","journal-title":"Science"},{"key":"ref14\/cit14b","doi-asserted-by":"crossref","first-page":"2433","DOI":"10.1021\/jo982239s","volume":"64","author":"Mark\u00f3 I. E.","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref14\/cit14c","doi-asserted-by":"crossref","first-page":"4343","DOI":"10.1016\/S0040-4039(00)00620-1","volume":"41","author":"Betzemeier B.","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref15\/cit15a","doi-asserted-by":"crossref","first-page":"5322","DOI":"10.1039\/b509167e","author":"Wang N.","year":"2005","journal-title":"Chem. Commun."},{"key":"ref15\/cit15b","doi-asserted-by":"crossref","first-page":"2679","DOI":"10.1002\/chem.200701818","volume":"14","author":"Wang X.","year":"2008","journal-title":"Chem.\u2014Eur. J."},{"key":"ref15\/cit15c","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1002\/adsc.200800501","volume":"351","author":"He X.","year":"2009","journal-title":"Adv. Synth. Catal."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"4112","DOI":"10.1021\/ja031765k","volume":"126","author":"Liu R.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"2849","DOI":"10.1002\/anie.200705347","volume":"47","author":"Shapiro N.","year":"2008","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref18\/cit18a","doi-asserted-by":"crossref","first-page":"2958","DOI":"10.1021\/jo00273a034","volume":"54","author":"Bisseret P.","year":"1989","journal-title":"J. Org. Chem."},{"key":"ref18\/cit18b","doi-asserted-by":"crossref","first-page":"6348","DOI":"10.1021\/ja00173a024","volume":"112","author":"Roush W. R.","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19","unstructured":"For recent development on enantioselective P-3CRs, see:"},{"key":"ref19\/cit19a","first-page":"7824","volume":"125","author":"Denmark S.","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19b","doi-asserted-by":"crossref","first-page":"9667","DOI":"10.1021\/jo050549m","volume":"70","author":"Denmark S.","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref19\/cit19c","doi-asserted-by":"crossref","first-page":"4021","DOI":"10.1021\/ol035010u","volume":"5","author":"Kusebauch U.","year":"2003","journal-title":"Org. Lett."},{"key":"ref19\/cit19d","doi-asserted-by":"crossref","first-page":"4231","DOI":"10.1021\/ol0482893","volume":"6","author":"Andreana P. R.","year":"2004","journal-title":"Org. Lett."},{"key":"ref19\/cit19e","first-page":"6","volume":"407","author":"Wang S.-X.","year":"2007","journal-title":"Eur. J. Org. Chem."},{"key":"ref19\/cit19f","doi-asserted-by":"crossref","first-page":"3615","DOI":"10.1021\/ol7014658","volume":"9","author":"Wang S.-X.","year":"2007","journal-title":"Org. Lett."},{"key":"ref19\/cit19g","doi-asserted-by":"crossref","first-page":"388","DOI":"10.1002\/anie.200704315","volume":"47","author":"Wang S.-X.","year":"2008","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref19\/cit19h","doi-asserted-by":"crossref","first-page":"9454","DOI":"10.1002\/anie.200804213","volume":"47","author":"Yue T.","year":"2008","journal-title":"Angew. Chem. Int. Ed"},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"947","DOI":"10.1002\/anie.200704840","volume":"47","author":"Grassot J.-M.","year":"2008","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref21\/cit21","unstructured":"X-ray structure of CuBr2\u2212Tempo complex:"},{"key":"ref21\/cit21a","doi-asserted-by":"crossref","first-page":"2307","DOI":"10.1021\/ja00215a055","volume":"110","author":"Caneschin A.","year":"1988","journal-title":"J. Am. Chem. Soc."},{"key":"ref21\/cit21b","doi-asserted-by":"crossref","first-page":"4474","DOI":"10.1021\/ic00023a039","volume":"30","author":"Laugier J.","year":"1991","journal-title":"Inorg. Chem."},{"key":"ref22\/cit22","unstructured":"Note that isocyanides can undergo a number of competitive reactions in the presence of cupric chloride under aerobic conditions."},{"key":"ref22\/cit22a","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1246\/bcsj.43.275","volume":"43","author":"Saegusa T.","year":"1970","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref22\/cit22b","doi-asserted-by":"crossref","first-page":"1217","DOI":"10.1139\/v69-196","volume":"47","author":"Saegusa T.","year":"1969","journal-title":"Can. J. Chem."},{"key":"ref22\/cit22c","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1016\/S0040-4039(00)90541-0","author":"Saegusa T.","year":"1967","journal-title":"Tetrahedron Lett."},{"key":"ref22\/cit22d","first-page":"3","volume":"127","author":"Saegusa T.","year":"1967","journal-title":"Tetrahedron Lett."},{"key":"ref22\/cit22dd","unstructured":"Control experiments have shown that mixing the benzyl isocyanide and CuCl2in toluene under oxygen atmosphere led to the complete decomposition of the former after 20 h. Therefore, to guarantee the success of the present domino oxidation\/P-3CR, the oxidation of alcohol to aldehyde and its subsequent P-3CR had to be faster than these competitive reactions. We found that polymerization of isocyanide was the main side reaction. However, in initial condition surveys, oxidation of isocyanide to isocyanate was also observed."},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"2209","DOI":"10.1002\/adsc.200900285","volume":"351","author":"Miao C.-X.","year":"2009","journal-title":"Adv. Synth Catal."},{"key":"ref24\/cit24","unstructured":"For mechanistic discussion on the Cu\u2212Tempo-catalyzed aerobic oxidation, see:"},{"key":"ref24\/cit24a","doi-asserted-by":"crossref","first-page":"3374","DOI":"10.1021\/ja00323a064","volume":"106","author":"Semmelhack M. F.","year":"1984","journal-title":"J. Am. Chem. Soc."},{"key":"ref24\/cit24b","doi-asserted-by":"crossref","first-page":"1119","DOI":"10.1016\/S0040-4039(00)84193-3","volume":"27","author":"Semmelhack M. F.","year":"1986","journal-title":"Tetrahedron Lett."},{"key":"ref24\/cit24c","doi-asserted-by":"crossref","first-page":"3232","DOI":"10.1039\/b305941c","volume":"1","author":"Dijiksman A.","year":"2003","journal-title":"Org. Biomol. Chem."},{"key":"ref24\/cit24d","doi-asserted-by":"crossref","first-page":"4790","DOI":"10.1002\/anie.200704292","volume":"47","author":"Galli C.","year":"2008","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref24\/cit24dd","unstructured":"See also ref20."},{"key":"ref25\/cit25","unstructured":"The reaction of2a,3a, and4ain the absence of CuCl2[TEMPO (0.15 equiv), NaNO2(0.15 equiv), O2, in toluene (C2.5 M), rt] led to 50% conversion of alcohol."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"1308","DOI":"10.1039\/b507657a","volume":"29","author":"Astolfi P.","year":"2005","journal-title":"New J. Chem."},{"key":"ref27\/cit27","unstructured":"MCRs of in situ generated isocyanides:"},{"key":"ref27\/cit27a","doi-asserted-by":"crossref","first-page":"3024","DOI":"10.1039\/b908541f","volume":"7","author":"El Kaim L.","year":"2009","journal-title":"Org. Biomol. Chem."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol100012y","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,15]],"date-time":"2023-03-15T17:05:56Z","timestamp":1678899956000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol100012y"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,3,10]]},"references-count":99,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2010,4,2]]}},"alternative-id":["10.1021\/ol100012y"],"URL":"https:\/\/doi.org\/10.1021\/ol100012y","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2010,3,10]]}}}