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Volumn 22, Issue 9, 2011, Pages 986-991

Synthesis of planar chiral pseudo-ortho-substituted aryl[2.2] paracyclophanes by stepwise successive palladium-catalyzed coupling reactions

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PARACYCLOPHANE DERIVATIVE;

EID: 79960965293     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.05.023     Document Type: Article
Times cited : (13)

References (66)
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    • For investigations on the influence of the substitution pattern on asymmetric induction, see: (a) Bolm, C.; Whelligan, D. K. Adv. Synth. Catal. 2006, 348, 2093-2100;
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    • For examples of trisubstituted [2.2]paracyclophanes, see
    • For examples of trisubstituted [2.2]paracyclophanes, see: (a) Xin, D.; Ma, Y.; He, F. Tetrahedron: Asymmetry 2010, 21, 333-338;
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    • For examples of [2.2]paracyclophane with a central chirality on an ethano bridge, see
    • For examples of [2.2]paracyclophane with a central chirality on an ethano bridge, see: Hou, X.-L.; Wu, X.-W.; Dai, L.-X.; Cao, B.-X.; Sun, J. Chem. Commun. 2000, 1195-1196.
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    • For examples of the catalytic single coupling of pseudo-orthodibromo[ 2.2]paracyclophane, see
    • For examples of the catalytic single coupling of pseudo-orthodibromo[ 2.2]paracyclophane, see: (a) Rozenberg, V. I.; Antonov, D. Y.; Zhuravsky, R. P.; Vorontsov, E. V.; Starikova, Z. A. Tetrahedron Lett. 2003, 44, 3801-3804;
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    • Ref. 3b
    • (d) Ref. 3b.
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    • (a) For selected reviews of organocatalysis, see: (a) Special Issue: Asymmetric Organocatalysis. Acc. Chem. Res. 2004, 37, 487-631.;
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    • There are only a few examples of organocatalysts based on a [2.2]paracyclophane backbone
    • There are only a few examples of organocatalysts based on a [2.2]paracyclophane backbone: (a) Braddock, D. C.; MacGilp, I. D.; Perry, B. G. Adv. Synth. Catal. 2004, 346, 1117-1130;
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    • Ref. 13c.; The use of chiral cyclophanyl phosphine as a reagent for the kinetic resolution of hydroperoxides has been reported by
    • (d) Ref. 13c.; The use of chiral cyclophanyl phosphine as a reagent for the kinetic resolution of hydroperoxides has been reported by:
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    • For syntheses of pseudo-ortho-substituted aryl[2.2]paracyclophanes with the axial chirality of the biaryl fragment, see
    • For syntheses of pseudo-ortho-substituted aryl[2.2]paracyclophanes with the axial chirality of the biaryl fragment, see: (a) Rosenberg, V.; Zhuravsky, R.; Sergeeva, E. Chirality 2006, 18, 95-102;
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    • Ref. 13a
    • (b) Ref. 13a.
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    • note
    • p)-4.
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    • To the best of our knowledge, no systematic study of the palladium-catalyzed amination of haloaryl triflates has been reported. Buchwald et al. demonstrated that in the reaction of bromoaryl nonaflates, the selective substitution of the nonaflate moiety could be achieved in good yields with use of BINAP ligand. However, they also reported that in the reaction of 4- bromophenyl nonaflate with aniline, the amine was selectively substituted for the bromide in preference to the nonaflate with use of (2-biphenyl)di- tertbutylphosphine as the ligand.
    • To the best of our knowledge, no systematic study of the palladium-catalyzed amination of haloaryl triflates has been reported. Buchwald et al. demonstrated that in the reaction of bromoaryl nonaflates, the selective substitution of the nonaflate moiety could be achieved in good yields with use of BINAP ligand. However, they also reported that in the reaction of 4- bromophenyl nonaflate with aniline, the amine was selectively substituted for the bromide in preference to the nonaflate with use of (2-biphenyl)di- tertbutylphosphine as the ligand. Anderson, K. W.; Mendez-Perez, M.; Priego, J.; Buchwald, S. L. J. Org. Chem. 2003, 68, 9563-9573.
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    • In the case of Suzuki-Miyaura coupling reaction, aryl triflates are known to be less reactive than the corresponding bromides
    • In the case of Suzuki-Miyaura coupling reaction, aryl triflates are known to be less reactive than the corresponding bromides. (a) Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201-2208.
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    • note
    • 3a this could be an alternative synthetic method for PHANEPHOS.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.