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Volumn , Issue 1, 2003, Pages 79-90

Synthesis of low generation phenylenealkylene dendrons as nonpolar building blocks for a dendrimer construction set

Author keywords

Building blocks; Dendrimers; Dendrons; Iododesilylation; Suzuki Miyaura cross coupling

Indexed keywords

ALKYLATION; MONOMERS; OLIGOMERS;

EID: 0037244515     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-36263     Document Type: Article
Times cited : (19)

References (70)
  • 2
    • 0003418177 scopus 로고    scopus 로고
    • Wiley, New York
    • For general information about dendrimers, see for example: (a) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons - Concepts, Syntheses, Applications; Wiley-VCH: Weinheim, 2001. (b) Dendrimers and other Dendritic Polymers; Fréchet, J. M. J.; Tomalia, D. A., Eds.; Wiley: New York, 2001.
    • (2001) Dendrimers and Other Dendritic Polymers
    • Fréchet, J.M.J.1    Tomalia, D.A.2
  • 3
    • 0001209856 scopus 로고    scopus 로고
    • For a review, see: Schlüter, A. D.; Rabe, J. P. Angew. Chem. 2000, 112, 860; Angew. Chem., Int. Ed. 2000, 39, 864.
    • (2000) Angew. Chem. , vol.112 , pp. 860
    • Schlüter, A.D.1    Rabe, J.P.2
  • 4
    • 0034599146 scopus 로고    scopus 로고
    • For a review, see: Schlüter, A. D.; Rabe, J. P. Angew. Chem. 2000, 112, 860; Angew. Chem., Int. Ed. 2000, 39, 864.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 864
  • 17
    • 84985535026 scopus 로고
    • See for example: (a) Xu, Z.; Moore, J. S. Acta Polym. 1994, 45, 83. (b) Bharati, P.; Patel, U.; Kawaguchi, T.; Pesak, D. J.; Moore, J. S. Macromolecules 1995, 28, 5955.
    • (1994) Acta Polym. , vol.45 , pp. 83
    • Xu, Z.1    Moore, J.S.2
  • 24
    • 33749292018 scopus 로고
    • Newcome, G. R.; Moorefield, C. N.; Baker, G. R.; Johnson, A. L.; Behera, R. K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1176; Angew. Chem. 1991, 103, 1205.
    • (1991) Angew. Chem. , vol.103 , pp. 1205
  • 25
    • 0037178547 scopus 로고    scopus 로고
    • In a similar approach phenylenealkylene dendrons with m-terphenylene branching units were constructed: Bo, Z.; Schlüter, A. D. J. Org. Chem. 2002, 67, 5327.
    • (2002) J. Org. Chem. , vol.67 , pp. 5327
    • Bo, Z.1    Schlüter, A.D.2
  • 28
    • 0035905441 scopus 로고    scopus 로고
    • (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. Angew. Chem., Int. Ed.; 2001, 40: 4544; Angew. Chem. 2001, 113, 4676.
    • (2001) Angew. Chem. , vol.113 , pp. 4676
  • 34
  • 35
    • 0346556817 scopus 로고    scopus 로고
    • note
    • Since TMS groups are not protective groups in the common sense, we prefer to use the term place holder, which precisely defines their function.
  • 37
    • 84942789598 scopus 로고
    • Wilkinson, G., Ed.; Pergamon: Oxford
    • (b) For an overview concerning hydroborations, see: Zaidlewicz, M. In Comprehensive Organometallic Chemistry, Vol. 7; Wilkinson, G., Ed.; Pergamon: Oxford, 1982, 143-160.
    • (1982) Comprehensive Organometallic Chemistry , vol.7 , pp. 143-160
    • Zaidlewicz, M.1
  • 38
    • 0347816989 scopus 로고    scopus 로고
    • note
    • Two-dimensional Heteronuclear Multiple Quantum Coherence NMR experiment.
  • 39
    • 0035780991 scopus 로고    scopus 로고
    • For recent overviews on(accelerated) convergent methods, see: (a) Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819. (b) Freeman, A. W.; Fréchet, J. M. J. Dendrimers and other Dendritic Polymers; Fréchet, J. M. J.; Tomalia, D. A., Eds.; Wiley: New York, 2001, 91-110.
    • (2001) Chem. Rev. , vol.101 , pp. 3819
    • Grayson, S.M.1    Fréchet, J.M.J.2
  • 40
    • 77953368299 scopus 로고    scopus 로고
    • Fréchet J. M. J.; Tomalia, D. A., Eds.; Wiley: New York
    • For recent overviews on(accelerated) convergent methods, see: (a) Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819. (b) Freeman, A. W.; Fréchet, J. M. J. Dendrimers and other Dendritic Polymers; Fréchet, J. M. J.; Tomalia, D. A., Eds.; Wiley: New York, 2001, 91-110.
    • (2001) Dendrimers and Other Dendritic Polymers , pp. 91-110
    • Freeman, A.W.1    Fréchet, J.M.J.2
  • 41
    • 0034813618 scopus 로고    scopus 로고
    • Recently a one-pot synthesis of an almost defect-free G4 dendron was reported: (a) Brauge, L.; Magro, G.; Caminade, A.-M; Majoral, J.-P. J. Am. Chem. Soc. 2001, 123, 6698. (b) Brauge, L.; Magro, G.; Caminade, A.-M.; Majoral, J.-P. J. Am. Chem. Soc. 2001, 123, 8446.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 6698
    • Brauge, L.1    Magro, G.2    Caminade, A.-M.3    Majoral, J.-P.4
  • 42
    • 85087577352 scopus 로고    scopus 로고
    • Recently a one-pot synthesis of an almost defect-free G4 dendron was reported: (a) Brauge, L.; Magro, G.; Caminade, A.-M; Majoral, J.-P. J. Am. Chem. Soc. 2001, 123, 6698. (b) Brauge, L.; Magro, G.; Caminade, A.-M.; Majoral, J.-P. J. Am. Chem. Soc. 2001, 123, 8446.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 8446
    • Brauge, L.1    Magro, G.2    Caminade, A.-M.3    Majoral, J.-P.4
  • 43
    • 0346556815 scopus 로고    scopus 로고
    • EP1013636, 2000
    • For 3,5-dibromoallylbenzene, see also: Ek, F.; Wistrand, L. G. EP1013636, 2000; Chem. Abstr. 2000, 133, 58600.
    • (2000) Chem. Abstr. , vol.133 , pp. 58600
    • Ek, F.1    Wistrand, L.G.2
  • 44
    • 0345925560 scopus 로고    scopus 로고
    • note
    • A more practical reason was the unfavorable synthesis protocol of the dibromo compound by Pd-catalyzed allylation of (3,5-dibromophenyl)trimethylstannane. In order to avoid the handling of tin compounds the diiodo analog was prepared by a different procedure.
  • 57
    • 0347816987 scopus 로고    scopus 로고
    • note
    • Target molecule 28 was also synthesized by reaction of the(expensive) 3,5-dibromobenzyl bromide with allylmagnesium bromide.
  • 58
    • 0000882877 scopus 로고    scopus 로고
    • See for example: (a) Jefferey, T. J. Chem. Soc., Chem. Commun. 1984, 1287. (b) Kang, S.-K.; Lee, H.-W.; Jang, S.-B.; Kim, T.-H.; Pyun, S.-J. J. Org. Chem. 1996, 61, 2604.
    • (1984) J. Chem. Soc., Chem. Commun. , pp. 1287
    • Jefferey, T.1
  • 60
    • 0000311321 scopus 로고    scopus 로고
    • The Suzuki-Miyaura cross-coupling of 34 with vinylic halides has been previously described: (a) Ridgway, B. H.; Woerpel, K. A. J. Org. Chem. 1998, 63, 458. (b) Trost, B. M.; Probst, G. D.; Schoop, A. J. Am. Chem. Soc. 1998, 120, 9228.
    • (1998) J. Org. Chem. , vol.63 , pp. 458
    • Ridgway, B.H.1    Woerpel, K.A.2
  • 61
    • 0032538014 scopus 로고    scopus 로고
    • The Suzuki-Miyaura cross-coupling of 34 with vinylic halides has been previously described: (a) Ridgway, B. H.; Woerpel, K. A. J. Org. Chem. 1998, 63, 458. (b) Trost, B. M.; Probst, G. D.; Schoop, A. J. Am. Chem. Soc. 1998, 120, 9228.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 9228
    • Trost, B.M.1    Probst, G.D.2    Schoop, A.3
  • 62
    • 0347816988 scopus 로고    scopus 로고
    • note
    • Preliminary investigations on the corresponding G3 dendron (not shown) encountered the additional problem that the molar mass of this molecule could not be confirmed, since the applied methods (EI, FAB, MALDI-TOF) only showed much smaller fragments. The mass spectral analyses of TBDMS-protected dendrons 3 and 4 point to the sensitivity of the silyl group with the loss of methyl and tert-butyl groups.
  • 64
    • 85088340125 scopus 로고    scopus 로고
    • note
    • 38
  • 70
    • 0346556813 scopus 로고    scopus 로고
    • note
    • No reference data were found.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.