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Volumn 41, Issue 8, 2011, Pages 1200-1207

FeCl3-mediated reaction of alkynols with iodine: An efficient and convenient synthetic route to vinyl iodides

Author keywords

Intramolecular iodoetherification; iron trichloride; vinyl iodide

Indexed keywords

1,2 DIIODO 3 METHYLPENT 1 EN 3 OL; 1,2 DIIODO 4 METHYLPENT 1 EN 3 OL; 2 (1 IODOPENTYLIDENE)TETRAHYDRO 2H PYRAN; 2,3 DIIODO 2 METHYLBUT 3 EN 2 OL; 2,3 DIIODO 3 PHENYLENPROP 2 EN 1 OL; 2,3 DIIODOBUT 2 EN 1 OL; 2,3 DIIODOHEX 2 EN 1 OL; 2,3 DIIODOOCT 2 EN 1 OL; 2,3 DIIODPROP 2 EN 1 OL; 3 (IODOMETHYLENE)TETRAHYDRO 2H PYRAN; 4 IODO 1H ISOCHROMENE; 4 IODO 2 METHYL 2,3 DIHYDROFURAN; 4 IODO 2 PHENYL 2,3 DIHYDROFURAN; 4 IODO 2,3 DIHYDROFURAN; 4 IODO 4 PROPYL 2,3 DIHYDROFURAN; 4 IODO 5 METHYL 2,3 DIHYDROFURAN; 5 ETHYL 4 IODO 2,3 DIHYDROFURAN; 5 IODO 2 PHENYL 3,4 DIHYDRO 2H PYRAN; ALKENE; ALKYNOL; FERROUS CHLORIDE; IODINE; UNCLASSIFIED DRUG; VINYL IODIDE DERIVATIVE;

EID: 79952913245     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.481739     Document Type: Article
Times cited : (18)

References (21)
  • 1
    • 11144323895 scopus 로고    scopus 로고
    • Iron-catalyzed reactions in organic synthesis
    • DOI 10.1021/cr040664h
    • For a recent reviews, see (a) Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Iron-catalyzed reactions in organic synthesis. Chem. Rev. 2004, 104, 6217-6254; (Pubitemid 40034050)
    • (2004) Chemical Reviews , vol.104 , Issue.12 , pp. 6217-6254
    • Bolm, C.1    Legros, J.2    Le Paih, J.3    Zani, L.4
  • 2
    • 20444365340 scopus 로고    scopus 로고
    • Advances in iron catalyzed cross-coupling reactions
    • Fü rstner, A.; Martin, R. Advances in iron catalyzed cross-coupling reactions. Chem. Lett. 2005, 34, 624; (b)
    • (2005) Chem. Lett. , vol.34 , pp. 624
    • Fürstner, A.1    Martin, R.2
  • 3
    • 44349129755 scopus 로고    scopus 로고
    • Iron-catalysed carbon-heteroatom and heteroatom- heteroatom bond-forming processes
    • Correa, A.; Mancheñ, O. J.; Bolm, C. Iron-catalysed carbon-heteroatom and heteroatom- heteroatom bond-forming processes. Chem. Soc. Rev. 2008, 37, 1108-1117; (c)
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1108-1117
    • Correa, A.1    Mancheñ, O.J.2    Bolm, C.3
  • 4
    • 50049109778 scopus 로고    scopus 로고
    • Sustainable metal catalysis with iron: From rustto a rising star
    • Enthaler, S.; Junge, K.; Beller, M. Sustainable metal catalysis with iron: From rustto a rising star. Angew. Chem., Int. Ed. 2008, 47, 3317-3321. (d)
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3317-3321
    • Enthaler, S.1    Junge, K.2    Beller, M.3
  • 5
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • For a recent reviews, see (a) Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483;
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 6
    • 0036589259 scopus 로고    scopus 로고
    • Aryl-aryl bond formation one century after the discovery of the Ullmann reaction
    • Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction. Chem. Rev. 2002, 102, 1359-1470; (b)
    • (2002) Chem. Rev. , vol.102 , pp. 1359-1470
    • Hassan, J.1    Sevignon, M.2    Gozzi, C.3    Schulz, E.4    Lemaire, M.5
  • 7
    • 0035905441 scopus 로고    scopus 로고
    • The B-alkyl suzuki-miyaura cross-coupling reaction: Development, mechanistic study, and applications in natural product synthesis
    • DOI 10.1002/1521-3773(20011217 )40:24<4544::AID-ANIE4544>3.0.CO;2-N
    • Chemler, S. R.; Trauner, D.; Danishefsky, S. J. The B-alkyl Suzuki-Miyaura cross-coupling reaction: Development, mechanistic study, and applications in natural product synthesis. Angew. Chem., Int. Ed. 2001, 40, 4544-4568; (c) (Pubitemid 34032185)
    • (2001) Angewandte Chemie - International Edition , vol.40 , Issue.24 , pp. 4544-4568
    • Chemler, S.R.1    Trauner, D.2    Danishefsky, S.J.3
  • 8
    • 0037112673 scopus 로고    scopus 로고
    • Palladium-catalyzed coupling reactions of aryl chlorides
    • DOI 10.1002/1521-3773(20021115) 41:22<4176::AID-ANIE4176>3.0.CO;2-U
    • Littke, A. F.; Fu, G. C. Palladium-catalyzed coupling reactions of aryl chlorides. Angew. Chem., Int. Ed. 2002, 41, 4176-4211; (d) (Pubitemid 35402094)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.22 , pp. 4176-4211
    • Littke, A.F.1    Fu, G.C.2
  • 9
    • 22744442306 scopus 로고    scopus 로고
    • Palladium-catalyzed cross-coupling reactions in total synthesis
    • DOI 10.1002/anie.200500368
    • Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Palladium-catalyzed cross-coupling reactions in total synthesis. Angew. Chem., Int. Ed. 2005, 44, 4442-4489; (e) (Pubitemid 41026385)
    • (2005) Angewandte Chemie - International Edition , vol.44 , Issue.29 , pp. 4442-4489
    • Nicolaou, K.C.1    Bulger, P.G.2    Sarlah, D.3
  • 10
    • 33645865241 scopus 로고    scopus 로고
    • On the nature of the active species in palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura couplings - Homogeneous or heterogeneous catalysis, a critical review
    • DOI 10.1002/adsc.200505473
    • Phan, N. T. S.; Sluys, M. V. D.; Jones, C. W. On the nature of the active species in palladium-catalyzed Mizoroki-Heck and Suzuki- Miyaura couplings-homogeneous or heterogeneous catalysis, a critical review. Adv. Synth. Catal. 2006, 348, 609-679; (f) (Pubitemid 43573698)
    • (2006) Advanced Synthesis and Catalysis , vol.348 , Issue.6 , pp. 609-679
    • Phan, N.T.S.1    Van Der Sluys, M.2    Jones, C.W.3
  • 11
    • 33845664895 scopus 로고    scopus 로고
    • Palladium-catalysed cross-coupling reactions on pyridazine moieties
    • DOI 10.1055/s-2006-951528
    • Nara, S.; Martinez, J.; Wermuth, C. G.; Parrot, I. Palladiumcatalysed cross-coupling reactions on pyridazine moieties. Synlett 2006, 3185-3204. (g) (Pubitemid 44951720)
    • (2006) Synlett , Issue.19 , pp. 3185-3204
    • Nara, S.1    Martinez, J.2    Wermuth, C.-G.3    Parrot, I.4
  • 12
    • 79952923603 scopus 로고    scopus 로고
    • Catalysts; John Wiley & Sons: Chichester, UK
    • Tsuji, J. Palladium Reagents and, Catalysts; John, Wiley & Sons: Chichester, UK, 2004;, 288-313.
    • (2004) Palladium Reagents and , pp. 288-313
    • Tsuji, J.1
  • 13
    • 0032537674 scopus 로고    scopus 로고
    • Organozinc mediated reactions
    • DOI 10.1016/S0040-4020(98)00318-4, PII S0040402098003184
    • For a recent review, see Knochel, P.; Perea, J. J. A.; Jones, P. Organozinc mediated reactions. Tetrahedron 1998, 54, 8275-8319. (Pubitemid 28294229)
    • (1998) Tetrahedron , vol.54 , Issue.29 , pp. 8275-8319
    • Knochel, P.1    Almena Perea, J.J.2    Jones, P.3
  • 16
    • 33846047998 scopus 로고    scopus 로고
    • Gold(I)-catalyzed intramolecular enantioselective hydroalkoxylation of allenes
    • DOI 10.1002/anie.200603260
    • Zhang, Z.; Widehoefer, R. A. Gold(I)-catalyzed intramolecular enantioselective hydroalkoxylation of allenes. Angew. Chem., Int. Ed. 2007, 46, 283-285; (a) (Pubitemid 46071718)
    • (2007) Angewandte Chemie - International Edition , vol.46 , Issue.1-2 , pp. 283-285
    • Zhang, Z.1    Widenhoefer, R.A.2
  • 17
    • 22944485617 scopus 로고    scopus 로고
    • Some typical advances in the synthetic applications of allenes
    • DOI 10.1021/cr020024j
    • Ma, S. Some typical advances in the synthetic applications of allenes. Chem. Rev. 2005, 105, 2829-2871. (b) (Pubitemid 41046992)
    • (2005) Chemical Reviews , vol.105 , Issue.7 , pp. 2829-2871
    • Ma, S.1
  • 18
    • 28044442286 scopus 로고    scopus 로고
    • An efficient synthesis of coumestrol and coumestans by iodocyclization and Pd-catalyzed intramolecular lactonization
    • DOI 10.1021/jo0517038
    • Yao,T.;Yue,D.;Rarock, R.C.An efficient synthesisof coumestrol and coumestans by iodocyclization and Pd-catalyzed intramolecular lactonization. J. Org. Chem. 2005, 70, 9985-9989; (a) (Pubitemid 41689164)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.24 , pp. 9985-9989
    • Yao, T.1    Yue, D.2    Larock, R.C.3
  • 19
    • 28744458426 scopus 로고    scopus 로고
    • Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization
    • DOI 10.1021/jo051299c
    • Yao, T.; Yue, D.; Rarock, R. C. Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization. J. Org. Chem. 2005, 70, 10292-10296; (b) (Pubitemid 41759898)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.25 , pp. 10292-10296
    • Yue, D.1    Yao, T.2    Larock, R.C.3
  • 20
    • 41649118478 scopus 로고    scopus 로고
    • Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols
    • DOI 10.1021/jo800088y
    • Arimitsu, S.; Jacobsen, J.M.; Hammond, G. B. Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols. J. Org. Chem. 2008, 73, 2886-2889. (c) (Pubitemid 351483002)
    • (2008) Journal of Organic Chemistry , vol.73 , Issue.7 , pp. 2886-2889
    • Arimitsu, S.1    Jacobsen, J.M.2    Hammond, G.B.3


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