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Volumn , Issue 1, 2006, Pages 51-68

Cu I-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective

Author keywords

Azides; Click chemistry; Cycloaddition; Heterocycles; Molecular diversity

Indexed keywords


EID: 84867726453     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500483     Document Type: Article
Times cited : (1578)

References (130)
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    • a) For a review of asymmetric 1,3-dipolar cycloaddition reactions, see: K. V. Gothelf, K. A. Jorgensen, Chem. Rev. 1998, 98, 863-909;
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    • For examples of uncatalyzed 1,3-cycloaddition reactions between azides and alkynes, see: a) A. R. Katritzky, S. K. Singh, J. Org. Chem. 2002, 67, 9077-9079;
    • (2002) J. Org. Chem. , vol.67 , pp. 9077-9079
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    • [21b]
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  • 85
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    • [40a]. For information on the dissolution of copper in aqueous systems and facilitation by amine hydrochloride salts, see: a) J. S. Thayer, Adv. Organomet. Chem. 1995, 38, 71-74;
    • (1995) Adv. Organomet. Chem. , vol.38 , pp. 71-74
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    • 29744470336 scopus 로고    scopus 로고
    • note
    • I iodide.
  • 91
    • 29744441032 scopus 로고    scopus 로고
    • note
    • Alkyne homocoupling may result in lower yields in some substrates; see below, section 3.4.1.
  • 100
    • 29744437853 scopus 로고    scopus 로고
    • note
    • For examples of unprotected alcohols that undergo click reactions without problem, see Table 1, Entries 2 and 3, and Table 5, Entry 4.
  • 103
    • 29744445038 scopus 로고    scopus 로고
    • note
    • The poor enantioselectivity observed for azide 39 may result from suprafacial [3,3] sigmatropic migration of the azido group, which would lead to racemization of the unconverted enantiomer.
  • 105
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    • For a recent review of microwave use in synthetic and combinatorial chemistry, see: C. O. Kappe, Angew. Chem. Int. Ed. 2004, 43, 6250-6284.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 6250-6284
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    • (Eds.: P. Lidström, J. P. Tierney), Blackwell, Oxford, Ch. 1
    • b) M. D. P. Mingos, in Microwave-Assisted Organic Synthesis (Eds.: P. Lidström, J. P. Tierney), Blackwell, Oxford, 2004, Ch. 1;
    • (2004) Microwave-Assisted Organic Synthesis
    • Mingos, M.D.P.1
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    • [59a]
    • [59a]; two reactions conducted under both microwave conditions and at room temperature afforded the desired product in almost identical yields, with microwave conditions only reducing reaction times.
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    • [26b]
    • [26b]).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.