메뉴 건너뛰기




Volumn 41, Issue 2, 2011, Pages 243-254

Inexpensive and efficient synthesis of propargylic substituted active methylene compounds catalyzed by FeCl3

Author keywords

Atom economical; carbon carbon bond; iron salt; propargylic alcohols; sustainable chemistry

Indexed keywords

1,3 DICARBONYL DERIVATIVE; CARBENE; CARBONYL DERIVATIVE; FERRIC CHLORIDE; UNCLASSIFIED DRUG;

EID: 78650257197     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903534031     Document Type: Article
Times cited : (27)

References (41)
  • 1
    • 4544298013 scopus 로고    scopus 로고
    • Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends
    • (a) Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends. Angew. Chem. Int. Ed. 2004, 43, 3368-3398;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3368-3398
    • Beller, M.1    Seayad, J.2    Tillack, A.3    Jiao, H.4
  • 2
    • 0037355249 scopus 로고    scopus 로고
    • Group-IV metal complexes as hydroamination catalysts
    • (b) Bytschkov, I.; Doye, S. Group-IV metal complexes as hydroamination catalysts. Eur. J. Org. Chem. 2003, 935-946;
    • (2003) Eur. J. Org. Chem. , pp. 935-946
    • Bytschkov, I.1    Doye, S.2
  • 3
    • 0034251445 scopus 로고    scopus 로고
    • Metal-catalyzed carbon-sulfur bond formation
    • (c) Kondo, T.; Mitsudo, T. Metal-catalyzed carbon-sulfur bond formation. Chem. Rev. 2000, 100, 3205- 3220;
    • (2000) Chem. Rev. , vol.100 , pp. 3205-3220
    • Kondo, T.1    Mitsudo, T.2
  • 4
    • 0034249725 scopus 로고    scopus 로고
    • Metal-catalyzed hydrostannations
    • (d) Smith, N. D.; Mancuso, J.; Lautens, M. Metal-catalyzed hydrostannations. Chem. Rev. 2000, 100, 3257-3284.
    • (2000) Chem. Rev. , vol.100 , pp. 3257-3284
    • Smith, N.D.1    Mancuso, J.2    Lautens, M.3
  • 7
    • 0004294109 scopus 로고
    • Viehe, H. G. (Ed.) Marcel Dekker: New York
    • (a) Viehe, H. G. (Ed.). Chemistry of Acetylenes; Marcel Dekker: New York, 1969;
    • (1969) Chemistry of Acetylenes
  • 9
    • 0037140714 scopus 로고    scopus 로고
    • The Nicholas reaction: The use of dicobalt hexacarbonyl-stabilised pro-pargylic cations in synthesis
    • (a) Teobald, B. J. The Nicholas reaction: The use of dicobalt hexacarbonyl-stabilised pro-pargylic cations in synthesis. Tetrahedron 2002, 58, 4133-4170;
    • (2002) Tetrahedron , vol.58 , pp. 4133-4170
    • Teobald, B.J.1
  • 10
    • 0034912138 scopus 로고    scopus 로고
    • Chemistry of propargyldicobalt cations recent developments in the Nicholas and related reactions
    • (b) Green, J. R. Chemistry of propargyldicobalt cations recent developments in the Nicholas and related reactions. Curr. Org. Chem. 2001, 5, 809-826.
    • (2001) Curr. Org. Chem. , vol.5 , pp. 809-826
    • Green, J.R.1
  • 11
    • 58949100680 scopus 로고    scopus 로고
    • Gold(III)-catalyzed direct nucleophilic substitution of propargylic alcohols
    • and references cited therein
    • (a) Georgy, M.; Boucard, V.; Debleds, O.; Zotto, C. D.; Campagne, J.-M. Gold(III)-catalyzed direct nucleophilic substitution of propargylic alcohols. Tetrahedron 2009, 65, 1758-1766, and references cited therein;
    • (2009) Tetrahedron , vol.65 , pp. 1758-1766
    • Georgy, M.1    Boucard, V.2    Debleds, O.3    Zotto, C.D.4    Campagne, J.-M.5
  • 12
    • 45349088383 scopus 로고    scopus 로고
    • Direct pro-pargylic substitution of hydroxyl group in propargylic alcohols
    • and references cited therein
    • (b) Kabalka, G. W.; Yao, M.-L. Direct pro-pargylic substitution of hydroxyl group in propargylic alcohols. Curr. Org. Synth. 2008, 5, 28-32, and references cited therein;
    • (2008) Curr. Org. Synth. , vol.5 , pp. 28-32
    • Kabalka, G.W.1    Yao, M.-L.2
  • 14
    • 33750309194 scopus 로고
    • Atom economy-A challenge for organic synthesis: Homogeneous catalysis leads the way
    • (a) Trost, B. M. Atom economy-A challenge for organic synthesis: Homogeneous catalysis leads the way. Angew. Chem. Int. Ed. 1995, 34, 259-281;
    • (1995) Angew. Chem. Int. Ed. , vol.34 , pp. 259-281
    • Trost, B.M.1
  • 15
    • 0026418434 scopus 로고
    • The atom economy: A search for synthetic efficiency
    • (b) Trost, B. M. The atom economy: A search for synthetic efficiency. Science 1991, 254, 1471-1477.
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.M.1
  • 16
    • 58949085347 scopus 로고    scopus 로고
    • Gold- and silver-catalyzed allylic alkylation of 1,3-dicarbonyl compounds with allylic alcohols
    • and references cited therein
    • (a) Kothandaraman, P.; Rao, W.; Zhang, X.; Chan, P. W. H. Gold- and silver-catalyzed allylic alkylation of 1,3-dicarbonyl compounds with allylic alcohols. Tetrahedron 2009, 65, 1833-1838, and references cited therein;
    • (2009) Tetrahedron , vol.65 , pp. 1833-1838
    • Kothandaraman, P.1    Rao, W.2    Zhang, X.3    Chan, P.W.H.4
  • 17
    • 34247850688 scopus 로고    scopus 로고
    • 3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions
    • 3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions. Tetrahedron Lett. 2007, 48, 4065-4069;
    • (2007) Tetrahedron Lett. , vol.48 , pp. 4065-4069
    • Jana, U.1    Biswas, S.2    Maiti, S.3
  • 19
    • 34547613570 scopus 로고    scopus 로고
    • Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid Brønsted acids
    • (d) Motokura, K.; Nakagiri, N.; Muzugaki, T.; Ebitani, K.; Kaneda, K. Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid Brønsted acids. J. Org. Chem. 2007, 72, 6006-6015;
    • (2007) J. Org. Chem. , vol.72 , pp. 6006-6015
    • Motokura, K.1    Nakagiri, N.2    Muzugaki, T.3    Ebitani, K.4    Kaneda, K.5
  • 20
    • 33947182489 scopus 로고    scopus 로고
    • Efficient metal-catalyzed direct benzylation and allylic alkylation of 2,4-pentanediones
    • (e) Reping, M.; Nachtsheim, B. J.; Kuenkel, A. Efficient metal-catalyzed direct benzylation and allylic alkylation of 2,4-pentanediones. Org. Lett. 2007, 9, 825-828;
    • (2007) Org. Lett. , vol.9 , pp. 825-828
    • Reping, M.1    Nachtsheim, B.J.2    Kuenkel, A.3
  • 21
    • 31444456960 scopus 로고    scopus 로고
    • A mild and direct indium-catalyzed process for the C-C bond formation from alcohols and active methylenes, alkoxyketones or indoles was developed
    • (f) Yasuda, M.; Somyo, T.; Baba, A. A mild and direct indium-catalyzed process for the C-C bond formation from alcohols and active methylenes, alkoxyketones or indoles was developed. Angew. Chem. Int. Ed. 2006, 45, 793-794.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 793-794
    • Yasuda, M.1    Somyo, T.2    Baba, A.3
  • 22
    • 34948852330 scopus 로고    scopus 로고
    • 3-catalyzed propargylation and alleny-lation of 1,3-dicarbonyl derivatives with propargylic alcohols: One-pot synthesis of multi-substituted furocoumarin
    • 3-catalyzed propargylation and alleny-lation of 1,3-dicarbonyl derivatives with propargylic alcohols: One-pot synthesis of multi-substituted furocoumarin. Tetrahedron 2007, 63, 11636-11643.
    • (2007) Tetrahedron , vol.63 , pp. 11636-11643
    • Huang, W.1    Wang, J.2    Shen, Q.3    Zhou, X.4
  • 23
    • 43849105745 scopus 로고    scopus 로고
    • Synthesis of tetrasubstituted furans via in-catalyzed propargylation of 1,3-dicarbonyl compounds-Cyclization tandem process
    • Feng, X.; Tan, Z.; Chen, D.; Shen, Y.; Guo, C.-C; Xiang, J.; Zhu, C. Synthesis of tetrasubstituted furans via in-catalyzed propargylation of 1,3-dicarbonyl compounds-Cyclization tandem process. Tetrahedron Lett. 2008, 49, 4110-4112.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 4110-4112
    • Feng, X.1    Tan, Z.2    Chen, D.3    Shen, Y.4    Guo, C.-C.5    Xiang, J.6    Zhu, C.7
  • 24
    • 33847795994 scopus 로고    scopus 로고
    • Brønsted acid-catalyzed propargylation of 1,3-dicarbonyl derivatives: Synthesis of tetrasubstituted furans
    • Sanz, R.; Miguel, D.; Mart́nez, A.; Alvarez-Gutierrez, J. M.; Rodŕguez, F. Brønsted acid-catalyzed propargylation of 1,3-dicarbonyl derivatives: Synthesis of tetrasubstituted furans. Org. Lett. 2007, 9, 727-730.
    • (2007) Org. Lett. , vol.9 , pp. 727-730
    • Sanz, R.1    Miguel, D.2    Mart́nez, A.3    Alvarez-Gutierrez, J.M.4    Rodŕguez, F.5
  • 25
    • 34547168331 scopus 로고    scopus 로고
    • A novel propargylation/cycloisomerization tandem process catalyzed by a ruthenium(II)/trifluoroacetic acid system: One-pot entry to fully substituted furans from readily available secondary propargylic alcohols and 1,3-dicarbonyl compounds
    • Cadierno, V.; Gimeno, J.; Noel, N. A novel propargylation/ cycloisomerization tandem process catalyzed by a ruthenium(II)/trifluoroacetic acid system: One-pot entry to fully substituted furans from readily available secondary propargylic alcohols and 1,3-dicarbonyl compounds. Adv. Synth. Catal. 2007, 349, 382-394.
    • (2007) Adv. Synth. Catal. , vol.349 , pp. 382-394
    • Cadierno, V.1    Gimeno, J.2    Noel, N.3
  • 26
    • 34948881697 scopus 로고    scopus 로고
    • Copper(II) triflate-catalyzed nucleophilic substitution of propargylic acetates with enox-ysilanes: A straightforward synthetic route to polysubstituted furans
    • Zhan, Z.-P.; Wang, S.-P.; Cai, X.-B.; Liu, H.-J.; Jing-liang, Y.; Yu, J.-L.; Cuia, Y.-Y. Copper(II) triflate-catalyzed nucleophilic substitution of propargylic acetates with enox-ysilanes: A straightforward synthetic route to polysubstituted furans. Adv. Synth. Catal. 2007, 349, 2097-2102.
    • (2007) Adv. Synth. Catal. , vol.349 , pp. 2097-2102
    • Zhan, Z.-P.1    Wang, S.-P.2    Cai, X.-B.3    Liu, H.-J.4    Jing-Liang, Y.5    Yu, J.-L.6    Cuia, Y.-Y.7
  • 29
    • 44349129755 scopus 로고    scopus 로고
    • Iron-catalyzed carbon-heteroatom and heteroatom-heteroatom bond-forming processes
    • (a) Correa, A.; Mencheno, O. G.; Bolm, C. Iron-catalyzed carbon-heteroatom and heteroatom-heteroatom bond-forming processes. Chem. Soc. Rev. 2008, 37, 1108-1117;
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1108-1117
    • Correa, A.1    Mencheno, O.G.2    Bolm, C.3
  • 30
    • 57549083398 scopus 로고    scopus 로고
    • The promise and challenge of iron-catalyzed cross coupling
    • (b) Sherry, B. D.; Frustner, A. The promise and challenge of iron-catalyzed cross coupling. Acc. Chem. Res. 2008, 41, 1500-1511;
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1500-1511
    • Sherry, B.D.1    Frustner, A.2
  • 31
    • 11144323895 scopus 로고    scopus 로고
    • Iron-catalyzed reactions in organic synthesis
    • (c) Bolm, C; Legros, J.; Paih, J. L.; Zani, L. Iron-catalyzed reactions in organic synthesis. Chem. Rev. 2004, 104, 6217-6254.
    • (2004) Chem. Rev. , vol.104 , pp. 6217-6254
    • Bolm, C.1    Legros, J.2    Paih, J.L.3    Zani, L.4
  • 32
    • 66149143042 scopus 로고    scopus 로고
    • New and efficient iron halide-mediated synthesis of alkenyl halides through coupling of alkynes and alcohols
    • (a) Biswas, S.; Maiti, S.; Jana, U. New and efficient iron halide-mediated synthesis of alkenyl halides through coupling of alkynes and alcohols. Eur. J. Org. Chem. 2009, 2354-2359;
    • (2009) Eur. J. Org. Chem. , pp. 2354-2359
    • Biswas, S.1    Maiti, S.2    Jana, U.3
  • 33
    • 56749104228 scopus 로고    scopus 로고
    • Iron(III)-catalyzed addition of benzylic alcohols to aryl alkynes-A new synthesis of substituted aryl ketones
    • (b) Jana, U.; Biswas, S.; Maiti, S. Iron(III)-catalyzed addition of benzylic alcohols to aryl alkynes-A new synthesis of substituted aryl ketones. Eur. J. Org. Chem. 2008, 5798-5804;
    • (2008) Eur. J. Org. Chem. , pp. 5798-5804
    • Jana, U.1    Biswas, S.2    Maiti, S.3
  • 34
    • 37649003787 scopus 로고    scopus 로고
    • An efficient FeCl3-catalyzed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or p-toluenesulfo-namide
    • (c) Jana, U.; Maiti, S.; Biswas, S. An efficient FeCl3-catalyzed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or p-toluenesulfo-namide. Tetrahedron Lett. 2008, 49, 858-862;
    • (2008) Tetrahedron Lett. , vol.49 , pp. 858-862
    • Jana, U.1    Maiti, S.2    Biswas, S.3
  • 35
    • 34548379937 scopus 로고    scopus 로고
    • 3-catalyzed highly C3-selective Friedel-Crafts alkylation of indoles with alcohols
    • 3-catalyzed highly C3-selective Friedel-Crafts alkylation of indoles with alcohols. Tetrahedron Lett. 2007, 48, 7160-7163.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 7160-7163
    • Jana, U.1    Maiti, S.2    Biswas, S.3
  • 37
    • 21244489719 scopus 로고    scopus 로고
    • An efficient and general iron-catalyzed arylation of benzyl alcohols and benzyl carboxylates
    • (b) Iovel, I.; Kristin, M.; Kischel, J.; Zapf, A.; Mathias, B. An efficient and general iron-catalyzed arylation of benzyl alcohols and benzyl carboxylates. Angew. Chem. Int. Ed. 2005, 44, 3913-3917.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3913-3917
    • Iovel, I.1    Kristin, M.2    Kischel, J.3    Zapf, A.4    Mathias, B.5
  • 39
    • 57649159510 scopus 로고    scopus 로고
    • 3-catalyzed propargylation-cycloisomerization tandem reaction: A facile one-pot synthesis of substituted furans
    • 3-catalyzed propargylation-cycloisomerization tandem reaction: A facile one-pot synthesis of substituted furans. Synlett. 2008, 3046-3052.
    • (2008) Synlett. , pp. 3046-3052
    • See Ji, W.-H.1    Pan, Y.-M.2    Zhao, S.-Y.3    Zhan, Z.-P.4
  • 40
    • 0345966676 scopus 로고
    • P. G. Sammes (Ed.) Pergamon: Oxford
    • Staunton, J. Comprehensive Organic Chemistry; P. G. Sammes (Ed.); Pergamon: Oxford, 1979, vol. 4, pp. 651-653.
    • (1979) Comprehensive Organic Chemistry , vol.4 , pp. 651-653
    • Staunton, J.1
  • 41
    • 7044235263 scopus 로고    scopus 로고
    • Domino reactions in organic synthesis
    • Tietze, L. F. Domino reactions in organic synthesis. Chem. Rev. 1996, 96, 115-136.
    • (1996) Chem. Rev. , vol.96 , pp. 115-136
    • Tietze, L.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.