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Volumn 10, Issue , 2014, Pages 384-393

Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions

Author keywords

Alkynes; Decarboxylative couplings; Erlotinib; Palladium; Propiolic acid

Indexed keywords


EID: 84894336266     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.10.36     Document Type: Article
Times cited : (22)

References (82)
  • 1
    • 33947727055 scopus 로고    scopus 로고
    • The Sonogashira reaction: A booming methodology in synthetic organic chemistry
    • DOI 10.1021/cr050992x
    • Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874-922. doi:10.1021/cr050992x (Pubitemid 46504819)
    • (2007) Chemical Reviews , vol.107 , Issue.3 , pp. 874-922
    • Chinchilla, R.1    Najera, C.2
  • 2
    • 33846688751 scopus 로고    scopus 로고
    • Palladium-based catalytic systems for the synthesis of conjugated enynes by sonogashira reactions and related alkynylations
    • DOI 10.1002/anie.200602761
    • Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834-871. doi:10.1002/anie.200602761 (Pubitemid 46192033)
    • (2007) Angewandte Chemie - International Edition , vol.46 , Issue.6 , pp. 834-871
    • Doucet, H.1    Hierso, J.-C.2
  • 3
    • 0037943974 scopus 로고    scopus 로고
    • doi:10.1021/cr020377i
    • Negishi, E.-i.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2018. doi:10.1021/cr020377i
    • (2003) Chem. Rev. , vol.103 , pp. 1979-2018
    • Negishi, E.-i.1    Anastasia, L.2
  • 5
    • 0001545058 scopus 로고
    • doi:10.1016/S0022-328X(00)94048-8
    • Cassar, L. J. Organomet. Chem. 1975, 93, 253-257. doi:10.1016/S0022- 328X(00)94048-8
    • (1975) Organomet. Chem. , vol.93 , pp. 253-257
    • Cassar, L.J.1
  • 10
    • 73249138889 scopus 로고    scopus 로고
    • doi:10.1021/cr900149d
    • Liu, J.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2009, 109, 5799-5867. doi:10.1021/cr900149d
    • (2009) Chem. Rev. , vol.109 , pp. 5799-5867
    • Liu, J.1    Lam, J.W.Y.2    Tang, B.Z.3
  • 12
    • 0142214753 scopus 로고    scopus 로고
    • A fluorescent self-amplifying wavelength-responsive sensory polymer for fluoride ions
    • DOI 10.1002/anie.200352075
    • Kim, T.-H.; Swager, T. M. Angew. Chem., Int. Ed. 2003, 42, 4803-4806. doi:10.1002/anie.200352075 (Pubitemid 37314612)
    • (2003) Angewandte Chemie - International Edition , vol.42 , Issue.39 , pp. 4803-4806
    • Kim, T.-H.1    Swager, T.M.2
  • 15
    • 34547617739 scopus 로고    scopus 로고
    • Palladium-catalyzed copper-free sonogashira coupling reaction in water and acetone
    • DOI 10.1055/s-2007-984533
    • Shi, S.; Zhang, Y. Synlett 2007, 1843-1850. doi:10.1055/s-2007-984533 (Pubitemid 47204130)
    • (2007) Synlett , Issue.12 , pp. 1843-1850
    • Shi, S.1    Zhang, Y.2
  • 21
    • 34247276500 scopus 로고    scopus 로고
    • doi101016/jtet2007.03.111
    • Cai, M.; Sha, J.; Xu, Q. Tetrahedron 2007, 63, 4642-4647. doi:10.1016/j.tet.2007.03.111
    • (2007) Tetrahedron , vol.63 , pp. 4642-4647
    • Cai, M.1    Sha, J.2    Xu, Q.3
  • 22
    • 24344438929 scopus 로고    scopus 로고
    • doi101016/jtet2005.06.119
    • Corma, A.; García, H.; Leyva, A. Tetrahedron 2005, 61, 9848-9854. doi:10.1016/j.tet.2005.06.119
    • (2005) Tetrahedron , vol.61 , pp. 9848-9854
    • Corma, A.1    García, H.2    Leyva, A.3
  • 27
    • 2342583283 scopus 로고    scopus 로고
    • Palladium-free and ligand-free Sonogashira cross-coupling
    • DOI 10.1039/b401586j
    • Thathagar, M. B.; Beckers, J.; Rothenberg, G. Green Chem. 2004, 6, 215-218. doi:10.1039/b401586j (Pubitemid 38591822)
    • (2004) Green Chemistry , vol.6 , Issue.4 , pp. 215-218
    • Thathagar, M.B.1    Beckers, J.2    Rothenberg, G.3
  • 28
  • 32
    • 34447299715 scopus 로고    scopus 로고
    • Rapid and highly selective copper-free sonogashira coupling in high-pressure, high-temperature water in a microfluidic system
    • DOI 10.1002/anie.200700611
    • Kawanami, H.; Matsushima, K.; Sato, M.; Ikushima, Y. Angew. Chem., Int. Ed. 2007, 46, 5129-5132. doi:10.1002/anie.200700611 (Pubitemid 47051271)
    • (2007) Angewandte Chemie - International Edition , vol.46 , Issue.27 , pp. 5129-5132
    • Kawanami, H.1    Matsushima, K.2    Sato, M.3    Ikushima, Y.4
  • 33
    • 33845246147 scopus 로고    scopus 로고
    • A copper- And amine-free sonogashira reaction of aryl halides catalyzed by 1,3,5-triaza-7-phosphaadamantane palladium systems
    • DOI 10.1021/om060636k
    • Ruiz, J.; Cutillas, N.; López, F.; López, G.; Bautista, D. Organometallics 2006, 25, 5768-5773. doi:10.1021/om060636k (Pubitemid 44865658)
    • (2006) Organometallics , vol.25 , Issue.24 , pp. 5768-5773
    • Ruiz, J.1    Cutillas, N.2    Lopez, F.3    Lopez, G.4    Bautista, D.5
  • 34
    • 31144473888 scopus 로고    scopus 로고
    • Modified palladium-catalyzed Sonogashira cross-coupling reactions under copper-, amine-, and solvent-free conditions
    • DOI 10.1021/jo051882t
    • Liang, Y.; Xie, Y.-X.; Li, J.-H. J. Org. Chem. 2006, 71, 379-381. doi:10.1021/jo051882t (Pubitemid 43128103)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.1 , pp. 379-381
    • Liang, Y.1    Xie, Y.-X.2    Li, J.-H.3
  • 37
    • 4043066278 scopus 로고    scopus 로고
    • Ligand-, copper-, and amine-free sonogashira reaction of aryl iodides and bromides with terminal alkynes
    • DOI 10.1021/jo049325e
    • Urgaonkar, S.; Verkade, J. G. J. Org. Chem. 2004, 69, 5752-5755. doi:10.1021/jo049325e (Pubitemid 39079634)
    • (2004) Journal of Organic Chemistry , vol.69 , Issue.17 , pp. 5752-5755
    • Urgaonkar, S.1    Verkade, J.G.2
  • 39
    • 0344944884 scopus 로고    scopus 로고
    • Efficient and general protocol for the copper-free sonogashira coupling of aryl bromides at room temperature
    • DOI 10.1021/ol035632f
    • Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191-4194. doi:10.1021/ol035632f (Pubitemid 37449622)
    • (2003) Organic Letters , vol.5 , Issue.22 , pp. 4191-4194
    • Soheili, A.1    Albaneze-Walker, J.2    Murry, J.A.3    Dormer, P.G.4    Hughes, D.L.5
  • 41
    • 0033678083 scopus 로고    scopus 로고
    • doi:10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.C O;2-X
    • Böhm, V. P. W.; Hermann, W. A. Eur. J. Org. Chem. 2000, 3679-3681. doi:10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.C O;2-X
    • (2000) Eur. J. Org. Chem. , pp. 3679-3681
    • Böhm, V.P.W.1    Hermann, W.A.2
  • 42
  • 45
  • 46
    • 12344289263 scopus 로고    scopus 로고
    • Tandem Sonogashira coupling: An efficient tool for the synthesis of diarylalkynes
    • DOI 10.1021/ol047983f
    • Novák, Z.; Nemes, P.; Kotschy, A. Org. Lett. 2004, 6, 4917-4920. doi:10.1021/ol047983f (Pubitemid 40125842)
    • (2004) Organic Letters , vol.6 , Issue.26 , pp. 4917-4920
    • Novak, Z.1    Nemes, P.2    Kotschy, A.3
  • 48
    • 84877124826 scopus 로고    scopus 로고
    • doi:10.1021/jo400574d
    • Li, X.; Yang, F.; Wu, Y. J. Org. Chem. 2013, 78, 4543-4550. doi:10.1021/jo400574d
    • (2013) J. Org. Chem. , vol.78 , pp. 4543-4550
    • Li, X.1    Yang, F.2    Wu, Y.3
  • 50
    • 84865208087 scopus 로고    scopus 로고
    • doi:10.1039/c2ob25643f
    • Zhao, B. Org. Biomol. Chem. 2012, 10, 7108-7119. doi:10.1039/c2ob25643f
    • (2012) Org. Biomol. Chem. , vol.10 , pp. 7108-7119
    • Zhao, B.1
  • 58
    • 77953901966 scopus 로고    scopus 로고
    • doi:10.1039/c0cc00403k
    • Feng, C.; Loh, T. P. Chem. Commun. 2010, 46, 4779-4781. doi:10.1039/c0cc00403k
    • (2010) Chem. Commun. , vol.46 , pp. 4779-4781
    • Feng, C.1    Loh, T.P.2
  • 60
    • 77951780267 scopus 로고    scopus 로고
    • doi:10.1021/ol1004615
    • Jia, W.; Jiao, N. Org. Lett. 2010, 12, 2000-2003. doi:10.1021/ol1004615
    • (2010) Org. Lett. , vol.12 , pp. 2000-2003
    • Jia, W.1    Jiao, N.2
  • 64
    • 64549098217 scopus 로고    scopus 로고
    • doi:10.1021/jo802290r
    • Moon, J.; Jang, M.; Lee, S. J. Org. Chem. 2009, 74, 1403-1406. doi:10.1021/jo802290r
    • (2009) J. Org. Chem. , vol.74 , pp. 1403-1406
    • Moon, J.1    Jang, M.2    Lee, S.3
  • 65
    • 72149117094 scopus 로고    scopus 로고
    • doi:10.1002/adsc.200900502
    • Kim, H.; Lee, P. H. Adv. Synth. Catal. 2009, 351, 2827-2832. doi:10.1002/adsc.200900502
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 2827-2832
    • Kim, H.1    Lee, P.H.2
  • 68
    • 33750035518 scopus 로고    scopus 로고
    • Catalytic enantioselective synthesis of adociacetylene B
    • DOI 10.1021/ol0615836
    • Trost, B. M.; Weiss, A. H. Org. Lett. 2006, 8, 4461-4464. doi:10.1021/ol0615836 (Pubitemid 44578652)
    • (2006) Organic Letters , vol.8 , Issue.20 , pp. 4461-4464
    • Trost, B.M.1    Weiss, A.H.2
  • 75
  • 78
    • 1442275477 scopus 로고    scopus 로고
    • Molecular crystals with moving parts: Synthesis, characterization, and crystal packing of molecular gyroscopes with methyl-substituted triptycyl frames
    • DOI 10.1021/jo035517i
    • Godinez, C. E.; Zepeda, G.; Mortko, C. J.; Dang, H.; Garcia-Garibay, M. A. J. Org. Chem. 2004, 69, 1652-1662. doi:10.1021/jo035517i (Pubitemid 38280415)
    • (2004) Journal of Organic Chemistry , vol.69 , Issue.5 , pp. 1652-1662
    • Godinez, C.E.1    Zepeda, G.2    Mortko, C.J.3    Dang, H.4    Garcia-Garibay, M.A.5
  • 79
    • 0141856212 scopus 로고    scopus 로고
    • Sonogashira coupling using bulky palladium-phenanthryl imidazolium carbene catalysis
    • DOI 10.1021/ol035147k
    • Ma, Y.; Song, C.; Jiang, W.; Wu, Q.; Wang, Y.; Liu, X.; Andrus, M. B. Org. Lett. 2003, 5, 3317-3319. doi:10.1021/ol035147k (Pubitemid 37140702)
    • (2003) Organic Letters , vol.5 , Issue.18 , pp. 3317-3319
    • Ma, Y.1    Song, C.2    Jiang, W.3    Wu, Q.4    Wang, Y.5    Liu, X.6    Andrus, M.B.7
  • 80
    • 84982407326 scopus 로고
    • doi:10.1002/cber.19821151104
    • Mayr, H.; Halberstadt-Kausch, I. K. Chem. Ber. 1982, 115, 3479-3515. doi:10.1002/cber.19821151104
    • (1982) Chem. Ber. , vol.115 , pp. 3479-3515
    • Mayr, H.1    Halberstadt-Kausch, I.K.2
  • 82
    • 84894315192 scopus 로고    scopus 로고
    • During our study we found that Pd2(dba)3 afforded the best yield with m-bromoaniline, while Pd(OAc)2 provided better results for the other substrates
    • During our study we found that Pd2(dba)3 afforded the best yield with m-bromoaniline, while Pd(OAc)2 provided better results for the other substrates.


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