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Volumn 11, Issue 11, 2009, Pages 2245-2248

Optically active dinuclear palladium complexes containing a Pd-Pd bond: Preparation and enantioinduction ability in asymmetric ring-opening reactions

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EID: 66149164337     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900533h     Document Type: Article
Times cited : (61)

References (49)
  • 8
    • 0001770691 scopus 로고
    • For representative papers dealing with dinuclear palladium complexes containing a Pd-Pd bond, see: a
    • For representative papers dealing with dinuclear palladium complexes containing a Pd-Pd bond, see: (a) Balch, A. L.; Benner, L. S. Inorg. Chem. 1982, 21, 47.
    • (1982) Inorg. Chem , vol.21 , pp. 47
    • Balch, A.L.1    Benner, L.S.2
  • 11
    • 0001929499 scopus 로고    scopus 로고
    • Many interesting reactions of dinuclear palladium complexes including catalytic reactions have been reported, a Benner, L. S, Olmstead, M. M, Hope, H, Balch, A. L. J. Organomet. Chem. 1978, 153, C31-C35
    • Many interesting reactions of dinuclear palladium complexes including catalytic reactions have been reported. (a) Benner, L. S.; Olmstead, M. M.; Hope, H.; Balch, A. L. J. Organomet. Chem. 1978, 153, C31-C35.
  • 30
    • 64349098905 scopus 로고    scopus 로고
    • and references cited therein
    • Denton, J. R.; Davies, H. M. L. Org. Lett. 2009, 11, 787-790, and references cited therein.
    • (2009) Org. Lett , vol.11 , pp. 787-790
    • Denton, J.R.1    Davies, H.M.L.2
  • 36
    • 66149176853 scopus 로고    scopus 로고
    • The chloride complex 1a was isolated as an orange powder that was proved to be a 57:43 mixture of two conformational isomers, and the bromide complex 1b isolated was a 90:10 mixture of two conformers. The iodide complex 1c was isolated as a single conformer.
    • The chloride complex 1a was isolated as an orange powder that was proved to be a 57:43 mixture of two conformational isomers, and the bromide complex 1b isolated was a 90:10 mixture of two conformers. The iodide complex 1c was isolated as a single conformer.
  • 37
    • 66149179056 scopus 로고    scopus 로고
    • The dihedral angle between the two Pd-square planes is approximately 40°. CCDC-718690 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
    • The dihedral angle between the two Pd-square planes is approximately 40°. CCDC-718690 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
  • 38
    • 0034104304 scopus 로고    scopus 로고
    • For representative papers dealing with asymmetric ring-opening reactions of oxabenzonorbornadienes and azabenzonorbornadienes, see: (a) Lautens, M, Renaud, J.-L, Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804-1805
    • For representative papers dealing with asymmetric ring-opening reactions of oxabenzonorbornadienes and azabenzonorbornadienes, see: (a) Lautens, M.; Renaud, J.-L.; Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804-1805.
  • 46
    • 66149189246 scopus 로고    scopus 로고
    • Carretero and co-workers generated cationic Pd complexes by treatment of palladium chloride complexes with NaB(ArF)4 or AgPF 6 and demonstrated their high catalytic activities in alkylative ring opening of oxabenzonorbornadienes and azabenzonorbornadienes. See refs 9d and 9e
    • 6 and demonstrated their high catalytic activities in alkylative ring opening of oxabenzonorbornadienes and azabenzonorbornadienes. See refs 9d and 9e.
  • 47
    • 66149164372 scopus 로고    scopus 로고
    • 31P NMR (161 MHz) δ-3.62
    • 31P NMR (161 MHz) δ-3.62
  • 48
    • 66149161699 scopus 로고    scopus 로고
    • A monocationic species was probably generated in the latter case
    • A monocationic species was probably generated in the latter case.
  • 49
    • 66149182926 scopus 로고    scopus 로고
    • In order to confirm the existence of a dimeric palladium species throughout the course of the reaction, we carried out the reaction in toluened8 using a stoichiometric amount of 1c/AgOTf 1:2, After the mixture was kept at 80 °C for 0.5 h, NaI was added. The 1H and 31P NMR spectra of the mixture showed almost the same signals as those of dimeric complex 1c
    • 31P NMR spectra of the mixture showed almost the same signals as those of dimeric complex 1c.


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