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Volumn 1, Issue 6, 2009, Pages 494-499

Metal-free carbon-carbon bond-forming reductive coupling between boronic acids and tosylhydrazones

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; CARBON; HYDRAZONE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

EID: 69249206655     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.328     Document Type: Article
Times cited : (310)

References (36)
  • 3
    • 58249108016 scopus 로고    scopus 로고
    • Domino iron catalysis: Direct aryl-alkyl cross-coupling
    • Czaplik, W. M., Mayer, M. & von Wangelin, A. J. Domino iron catalysis: direct aryl-alkyl cross-coupling. Angew. Chem. Int. Ed. 48, 607-610 (2009).
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 607-610
    • Czaplik, W.M.1    Mayer, M.2    Von Angelin, A.J.3
  • 4
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: Diverse chemical function from a few good reactions
    • Kolb, H. C., Finn, M. G. & Sharpless, K. B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004-2021 (2001).
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 5
    • 47649133089 scopus 로고    scopus 로고
    • Click chemistry and medicinal chemistry: A case of ?cyclo-addition?
    • Moorhouse, A. D. & Moses, J. E. Click chemistry and medicinal chemistry: a case of ?cyclo-addition?. ChemMedChem. 3, 715-723 (2008).
    • (2008) ChemMedChem. , vol.3 , pp. 715-723
    • Moorhouse, A.D.1    Moses, J.E.2
  • 6
    • 55049090701 scopus 로고    scopus 로고
    • Polymer ?clicking? by CuAAC reactions
    • Medal, M. Polymer ?clicking? by CuAAC reactions. Macromol. Rapid Commun. 29, 1016-1051 (2008).
    • (2008) Macromol. Rapid Commun. , vol.29 , pp. 1016-1051
    • Medal, M.1
  • 7
    • 58249110588 scopus 로고    scopus 로고
    • Dual labeling of biomolecules by using click chemistry: A sequential approach
    • Kele, P., Mezo, G., Achatz, D. Wolfdeis, O. S. Dual labeling of biomolecules by using click chemistry: a sequential approach. Angew. Chem. Int. Ed. 48, 344-347 (2009).
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 344-347
    • Kele, P.1    Mezo, G.2    Achatz, D.3    Wolfdeis, O.S.4
  • 8
    • 18144398606 scopus 로고    scopus 로고
    • The use of tosylhydrazone salts as a safe alternative for handling diazo compounds and their applications in organic synthesis
    • Fulton, J. R., Aggarwal, V. K. & de Vicente, J. The use of tosylhydrazone salts as a safe alternative for handling diazo compounds and their applications in organic synthesis. Eur. J. Org. Chem. 1479-1492 (2005).
    • (2005) Eur. J. Org. Chem. , pp. 1479-1492
    • Fulton, J.R.1    Aggarwal, V.K.2    De Vicente, J.3
  • 9
    • 0001004998 scopus 로고    scopus 로고
    • Catalytic cyclopropanation of alkenes using diazo compounds generated in situ
    • Aggarwal, V. K., de Vicente, J. & Bonnert, R. V. Catalytic cyclopropanation of alkenes using diazo compounds generated in situ. A novel route to 2-arylcyclopropylamines. Org. Lett. 3, 2785-2788 (2001).
    • (2001) Org. Lett. , vol.3 , pp. 2785-2788
    • Aggarwal, V.K.1    De Vicente, J.2    Bonnert, R.V.3
  • 10
    • 0035901657 scopus 로고    scopus 로고
    • Catalytic asymmetric synthesis of epoxides from aldehydes using sulfur ylides with in situ generation of diazocompounds
    • Aggarwal, V. K., Alonso, E., Hynd, G., Lydon, K. M., Palmer, M. J., Porcelloni, M. & Studley, J. R. Catalytic asymmetric synthesis of epoxides from aldehydes using sulfur ylides with in situ generation of diazocompounds. Angew. Chem. Int. Ed. 40, 1430-1433 (2001).
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1430-1433
    • Aggarwal, V.K.1    Alonso, E.2    Hynd, G.3    Lydon, K.M.4    Palmer, M.J.5    Porcelloni, M.6    Studley, J.R.7
  • 11
    • 0035901642 scopus 로고    scopus 로고
    • Application of chiral sulfides to catalytic asymmetric aziridination and cyclopropanation with in situ generation of the diazo compound
    • Aggarwal, V. K., Alonso, E., Fang, G., Ferrara, M., Hynd, G. & Porcelloni, M. Application of chiral sulfides to catalytic asymmetric aziridination and cyclopropanation with in situ generation of the diazo compound. Angew. Chem. Int. Ed. 40, 1433-1436 (2001).
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1433-1436
    • Aggarwal, V.K.1    Alonso, E.2    Fang, G.3    Ferrara, M.4    Hynd, G.5    Porcelloni, M.6
  • 12
    • 0141742604 scopus 로고    scopus 로고
    • Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles
    • Cheung, W.-H., Zheng, S.-L. Yu, W.-Y., Guo-Chuan Zhou, G.-C. & Che, C.-M. Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles. Org. Lett. 5, 2535-2538 (2003).
    • (2003) Org. Lett. , vol.5 , pp. 2535-2538
    • Cheung, W.-H.1    Zheng, S.-L.2    Yu, W.-Y.3    Guo-Chuan Zhou, G.-C.4    Che, C.-M.5
  • 13
    • 34547212241 scopus 로고    scopus 로고
    • N-Tosylhydrazones as reagents for cross-coupling reactions: A route to polysubstituted olefins
    • Barluenga, J., Moriel, P., Valdés, C. & Aznar, F. N-Tosylhydrazones as reagents for cross-coupling reactions: a route to polysubstituted olefins. Angew. Chem. Int. Ed. 46, 5587-5590 (2007).
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5587-5590
    • Barluenga, J.1
  • 14
    • 0037682941 scopus 로고
    • Reductive alkylation of aldehyde tosylhydrazones with organolithium reagents
    • Vedejs, E. & Stolle, W. T. Reductive alkylation of aldehyde tosylhydrazones with organolithium reagents. Tetrahedron Lett. 18, 135-138 (1977).
    • (1977) Tetrahedron Lett. , vol.18 , pp. 135-138
    • Vedejs, E.1    Stolle, W.T.2
  • 15
    • 0032475428 scopus 로고    scopus 로고
    • Highly efficient methodology for the reductive coupling of aldehyde tosylhydrazones with alkyllithium reagents
    • Myers, A. G. & Movassaghi, M. Highly efficient methodology for the reductive coupling of aldehyde tosylhydrazones with alkyllithium reagents. J. Am. Chem. Soc. 120, 8891-8892 (1998).
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 8891-8892
    • Myers, A.G.1    Movassaghi, M.2
  • 17
    • 0002958913 scopus 로고
    • The decomposition of toluene-psulfonylhydrazones by alkali.
    • Bamford, W. R. & Stevens, T. S. The decomposition of toluene-psulfonylhydrazones by alkali. J. Chem. Soc. 4735-4740 (1952).
    • (1952) J. Chem. Soc. , pp. 4735-4740
    • Bamford, W.R.1    Stevens, T.S.2
  • 18
    • 4544325184 scopus 로고    scopus 로고
    • Copper carbenoid mediated N-alkylation of imidazoles and its use in a novel synthesis of bifonazole
    • Cuevas-Yañez, E., Serrano, J. M., Huerta, G., Muchowsky, J. M. & Cruz- Almanza, R. Copper carbenoid mediated N-alkylation of imidazoles and its use in a novel synthesis of bifonazole. Tetrahedron 60, 9391-9396 (2004).
    • (2004) Tetrahedron , vol.60 , pp. 9391-9396
    • Cuevas-Yañez, E.1
  • 20
    • 2342470022 scopus 로고    scopus 로고
    • Identification of 4-(1H-imidazol-4(5)-ylmethyl)pyridine (Immethridine) as a novel, potent, and highly selective Histamine H3 receptor agonist
    • Kitbunnadaj, R. et al. Identification of 4-(1H-imidazol-4(5)-ylmethyl) pyridine (Immethridine) as a novel, potent, and highly selective Histamine H3 receptor agonist. J. Med. Chem. 47, 2414-2417 (2004).
    • (2004) J. Med. Chem. , vol.47 , pp. 2414-2417
    • Kitbunnadaj, R.1
  • 21
    • 2342561153 scopus 로고    scopus 로고
    • Rational design and synthesis of novel dimeric diketoacidcontaining inhibitors of HIV-1 Integrase: Implication for binding to two metal ions on the active site of integrase
    • Long, Y.-Q. et al. Rational design and synthesis of novel dimeric diketoacidcontaining inhibitors of HIV-1 Integrase: implication for binding to two metal ions on the active site of integrase. J. Med. Chem. 47, 2561-2573 (2004).
    • (2004) J. Med. Chem. , vol.47 , pp. 2561-2573
    • Long, Y.-Q.1
  • 22
    • 1542719135 scopus 로고    scopus 로고
    • Preliminary in vitro studies on two potent, water-soluble trimethoprim analogues with exceptional species selectivity against dihydrofolate reductase from Pneumocystis carinii and Mycobacterium avium
    • Forsch, R. A., Queener, S. F. & Rosowsky, A. Preliminary in vitro studies on two potent, water-soluble trimethoprim analogues with exceptional species selectivity against dihydrofolate reductase from Pneumocystis carinii and Mycobacterium avium. Bioorg. Med. Chem. Lett. 14, 1811-1815 (2004).
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 1811-1815
    • Forsch, R.A.1    Queener, S.F.2    Rosowsky, A.3
  • 23
    • 33847403082 scopus 로고    scopus 로고
    • Effect of substituents on diarylmethanes for antitubercular activity
    • Panda, G. et al. Effect of substituents on diarylmethanes for antitubercular activity. Eur. J. Med. Chem. 42, 410-419 (2007).
    • (2007) Eur. J. Med. Chem. , vol.42 , pp. 410-419
    • Panda, G.1
  • 24
    • 33751569703 scopus 로고    scopus 로고
    • Suzuki-Miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates
    • Molander, G. A. & Elia, M. D. Suzuki-Miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates. J. Org. Chem. 71, 9198-9202 (2006).
    • (2006) J. Org. Chem. , vol.71 , pp. 9198-9202
    • Molander, G.A.1    Elia, M.D.2
  • 25
    • 38349106240 scopus 로고    scopus 로고
    • Simple palladium(II) precatalyst for Suzuki-Miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners
    • Burns, M. J., Fairlamb, I. J. S., Kapdi, A. R., Sehnal, P. & Taylor, R. J. K. Simple palladium(II) precatalyst for Suzuki-Miyaura couplings: efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners. Org. Lett. 9, 5397-5400 (2007).
    • (2007) Org. Lett. , vol.9 , pp. 5397-5400
    • Burns, M.J.1    Fairlamb, I.J.S.2    Kapdi, A.R.3    Sehnal, P.4    Taylor, R.J.K.5
  • 26
    • 53849094479 scopus 로고    scopus 로고
    • One-pot dual substitutions of bromobenzyl chloride, 2-chloromethyl-6- halogenoimidazo[1, 2-a]pyridine and -[1, 2-b]pyridazine by Suzuki-Miyaura cross-coupling reactions
    • Henry, N., Enguehard-Gueiffier, C., Thery, I. & Gueiffier, A. One-pot dual substitutions of bromobenzyl chloride, 2-chloromethyl-6-halogenoimidazo[1, 2-a]pyridine and -[1, 2-b]pyridazine by Suzuki-Miyaura cross-coupling reactions. Eur. J. Org. Chem. 4824-4827 (2008).
    • (2008) Eur. J. Org. Chem. , pp. 4824-4827
    • Henry, N.1    Enguehard-Gueiffier, C.2    Thery, I.3    Gueiffier, A.4
  • 27
    • 0034595263 scopus 로고    scopus 로고
    • Traceless solid-phase synthesis of biarylmethane structures through Pd-catalyzed release of benzylsulfonium salts
    • Vanier, C., Lorgé, F., Wagner, A. & Mioskowski, C. Traceless solid-phase synthesis of biarylmethane structures through Pd-catalyzed release of benzylsulfonium salts. Angew. Chem. Int. Ed. 39, 1679-1682 (2000).
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1679-1682
    • Vanier, C.1
  • 28
    • 64549155326 scopus 로고    scopus 로고
    • Palladium-catalyzed crosscoupling reactions of benzyl indium reagents with aryl iodides
    • Chupak, L. S., Wolkowsky, J. P. & Chantigny, Y. A. Palladium-catalyzed crosscoupling reactions of benzyl indium reagents with aryl iodides. J. Org. Chem. 74, 1388-1390 (2009).
    • (2009) J. Org. Chem. , vol.74 , pp. 1388-1390
    • Chupak, L.S.1    Wolkowsky, J.P.2    Chantigny, Y.A.3
  • 29
    • 58649099580 scopus 로고    scopus 로고
    • Iron-catalysed Negishi coupling of benzyl halides and phosphates
    • Bedford, R. B., Huwe, M. Wilkinson, M. C. Iron-catalysed Negishi coupling of benzyl halides and phosphates. Chem. Commun. 600-602 (2009).
    • (2009) Chem. Commun. , pp. 600-602
    • Bedford, R.B.1    Huwe, M.2    Wilkinson, M.C.3
  • 30
    • 0001317550 scopus 로고
    • The reaction of trialkylboranes with diazoacetone. A new ketone synthesis
    • Hooz, J. & Linke, S. The reaction of trialkylboranes with diazoacetone. A new ketone synthesis. J. Am. Chem. Soc. 90, 5936-5937 (1968).
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5936-5937
    • Hooz, J.1    Linke, S.2
  • 31
    • 0000565492 scopus 로고
    • Reaction of dialkylchloroboranes with ethyl diazoacetate at low temperatures. Facile two-carbon homologation under exceptionally mild conditions
    • Brown, H. C., Midland, M. M. & Levy A. B. Reaction of dialkylchloroboranes with ethyl diazoacetate at low temperatures. Facile two-carbon homologation under exceptionally mild conditions. J. Am. Chem. Soc. 94, 3662-3664 (1972).
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 3662-3664
    • Brown, H.C.1    Midland, M.M.2    Levy, A.B.3
  • 32
    • 45849093273 scopus 로고    scopus 로고
    • Recent studies on the reactions of a-diazocarbonyl compounds
    • Zang, Z. & Wang, J. Recent studies on the reactions of a-diazocarbonyl compounds. Tetrahedron, 64, 6577-6605 (2008).
    • (2008) Tetrahedron , vol.64 , pp. 6577-6605
    • Zang, Z.1    Wang, J.2
  • 33
    • 38949204038 scopus 로고    scopus 로고
    • Palladium-catalyzed cross-coupling of a-diazocarbonyl compounds with arylboronic acids
    • Peng, C., Wang, Y. & Wang, J. Palladium-catalyzed cross-coupling of a-diazocarbonyl compounds with arylboronic acids. J. Am. Chem. Soc. 130, 1566-1567 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 1566-1567
    • Peng, C.1    Wang, Y.2    Wang, J.3
  • 34
    • 64349114463 scopus 로고    scopus 로고
    • Arylation and vinylation of adiazocarbonyl compounds with boroxines
    • Peng, C., Zhang, W., Yan, G. & and Wang, J. Arylation and vinylation of adiazocarbonyl compounds with boroxines. Org. Lett. 11, 1667-1670 (2009).
    • (2009) Org. Lett. , vol.11 , pp. 1667-1670
    • Peng, C.1    Zhang, W.2    Yan, G.3    Wang, J.4
  • 35
    • 0000304537 scopus 로고
    • An asymmetric synthesis of the diastereomeric 1-(2-cyclohexenyl)-1- alkanols in high optical purity via a stereochemically stable allylic borane, B-2- cyclohexen-1-yldiisopinocampheylborane
    • Brown, H. C., Jadhav, P. K. & Bhat, K. S. An asymmetric synthesis of the diastereomeric 1-(2-cyclohexenyl)-1-alkanols in high optical purity via a stereochemically stable allylic borane, B-2- cyclohexen-1- yldiisopinocampheylborane. J. Am. Chem. Soc. 107, 2564-2565 (1985).
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 2564-2565
    • Brown, H.C.1    Jadhav, P.K.2    Bhat, K.S.3
  • 36
    • 33846436053 scopus 로고    scopus 로고
    • Asymmetric synthesis of a-substituted allyl boranes and their application in the synthesis of iso-agatharesinol
    • Fang, G. Y. & Aggarwal, V. K. Asymmetric synthesis of a-substituted allyl boranes and their application in the synthesis of iso-agatharesinol. Angew. Chem. Int. Ed. 46, 359-362 (2007).
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 359-362
    • Fang, G.Y.1    Aggarwal, V.K.2


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