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Volumn 12, Issue 20, 2006, Pages 5267-5281

Synthesis, structure, and reactivity of palladacycles that contain a chiral rhenium fragment in the backbone: New cyclometalation and catalyst design strategies

Author keywords

Cyclometalation; Heck reaction; Palladacycie; Palladium; Rhenium; Suzuki coupling

Indexed keywords

CATALYSIS; COMPLEXATION; REACTION KINETICS; RHENIUM COMPOUNDS;

EID: 33745924989     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501540     Document Type: Article
Times cited : (30)

References (115)
  • 45
    • 33745929206 scopus 로고    scopus 로고
    • note
    • Compound numbers that are indexed a, b, and c indicate chloride, bromide, and iodide derivatives, respectively.
  • 51
    • 33745925156 scopus 로고    scopus 로고
    • Doctoral Dissertation, Universität Erlangen-Nürnberg
    • K. Kromm, Doctoral Dissertation, Universität Erlangen-Nürnberg, 2003.
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    • Kromm, K.1
  • 52
    • 33745904033 scopus 로고    scopus 로고
    • note
    • a) When both enantiomers were prepared, the synthesis of only one is given in the Experimental Section, b) Only (S,S)-10a, (R,R)-10c, and (R)-16 were prepared. The configurations of the last two are the opposite of those normally depicted in papers in this series. To facilitate comparisons, their configurations (and those of the necessary educts) have been inverted throughout this paper, c) The crystal structure of (R)-6c was determined, and not (S)-6c as represented throughout this paper.
  • 56
    • 33745893979 scopus 로고    scopus 로고
    • note
    • The only exception is (S,S)-13 below (δ = 4.78-5.54). Here, the crystal structure shows a distance of 4.145 Å between the centroid of the PPh3 phenyl ring syn to the cyclopentadienyl ligand and the closest cyclopentadienyl carbon (α to the Pd-C bond). In contrast, the three other crystallographically characterized palladacycles show distances of 3.735-3.878 Å.
  • 57
    • 33745874252 scopus 로고    scopus 로고
    • (Eds.: N. G. Connely, T. Damhus, R. M. Hartshorn, A. T. Hutton), Royal Society of Chemistry, London
    • The terms SP-4-2, SP-4-3, and SP-4-4 are used to distinguish the three stereoisomers of square planar complexes of formula MLL′L″L‴ (SP-4 = square planar; -2, -3, and -4 indicate that the groups with the second, third, or fourth highest Cahn-Ingold-Prelog priorities are trans to the group with the highest priority): Nomenclature of Inorganic Chemistry: IUPAC Recommendations 2005 (Eds.: N. G. Connely, T. Damhus, R. M. Hartshorn, A. T. Hutton), Royal Society of Chemistry, London, 2005, pp. 179-181.
    • (2005) Nomenclature of Inorganic Chemistry: IUPAC Recommendations 2005 , pp. 179-181
  • 66
    • 33745877007 scopus 로고    scopus 로고
    • note
    • 2 unit on one terminus is anti to the cyclopentadienyl unit on the other.
  • 76
    • 33644920912 scopus 로고    scopus 로고
    • For additional palladacycles that have been shown by other types of experimental data to give nonmolecular catalysts, see: a) J. G. de Vries, Dalton Trans 2006, 421;
    • (2006) Dalton Trans , pp. 421
    • De Vries, J.G.1
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    • 33745903755 scopus 로고    scopus 로고
    • Doctoral Dissertation, Universität Erlangen-Nürn-berg
    • F. K. Friedlein, Doctoral Dissertation, Universität Erlangen-Nürn-berg, 2006.
    • (2006)
    • Friedlein, F.K.1
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    • 33745915998 scopus 로고    scopus 로고
    • note
    • FAB, 3-NBA, m/z (%); the peaks correspond to the most intense signal of the isotope envelope.
  • 98
    • 33745920937 scopus 로고    scopus 로고
    • note
    • 2, toluene/hexanes (1:1 v/v)) was performed.
  • 99
    • 33745893381 scopus 로고    scopus 로고
    • note
    • 6.
  • 100
    • 33745906097 scopus 로고    scopus 로고
    • note
    • Measured gravimetrically inside a glove box (difference in mass between loaded and discharged syringe).
  • 101
    • 33745883419 scopus 로고    scopus 로고
    • note
    • 2 signals.
  • 102
    • 33745907991 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of (S,S)-10b and were assigned to the meso diastereomer.
  • 103
    • 33745892789 scopus 로고    scopus 로고
    • note
    • These (broadened) resonances were tentatively assigned to both syn and anti isomers (overlapping signals). However, in some cases non-overlapping signals of the minor isomer may have been be too broad or too weak to observe.
  • 104
    • 33745897777 scopus 로고    scopus 로고
    • note
    • 13C NMR signals were too weak to observe.
  • 105
    • 33745892539 scopus 로고    scopus 로고
    • note
    • It was not possible to assign signals to the RePPh3 vs PdPPh3 phenyl groups; the designations ilo/m/p and i′/oPrime;/m′/p′ are arbitrary.
  • 106
    • 33745917574 scopus 로고    scopus 로고
    • note
    • 2 phosphorus atom and the methyl group of the cis acetate ligand.
  • 107
    • 33745898690 scopus 로고    scopus 로고
    • Doctoral Dissertation, Universität Erlangen-Nürn-berg, The synthesis is analogous to that of the racemate.[9a]
    • S. Eichenseher, Doctoral Dissertation, Universität Erlangen-Nürn-berg, 2005. The synthesis is analogous to that of the racemate.[9a]
    • (2005)
    • Eichenseher, S.1
  • 108
    • 33745921074 scopus 로고    scopus 로고
    • 13C NMR signal was detected
    • 13C NMR signal was detected.
  • 109
    • 33745904323 scopus 로고    scopus 로고
    • note
    • This signal overlaps with one of (S,S)-10b. Therefore, the intensity reflects the theoretical rather than a measured value.
  • 110
    • 33745930676 scopus 로고    scopus 로고
    • note
    • When the crystals were dried by either vacuum or a nitrogen stream, the solvent of crystallization was removed.
  • 112
    • 0031059866 scopus 로고    scopus 로고
    • Macromolecular Crystallography, Part A, 307
    • b) "Scalepack" data processing software: Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276 (Macromolecular Crystallography, Part A), 307.
    • (1997) Methods in Enzymology , pp. 276
    • Otwinowski, Z.1    Minor, W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.