Unexpected isolation, and structural characterization, of a β-hydrogen-containing σ-alkylpalladium halide complex in the course of anintramolecular Heck reaction. Synthesis of polycyclic isoquinoline derivatives

Chemical Communications

Volumn 2, Issue , 2002, Pages 272-273

  Clique, Blandine ^a   Fabritius, Charles Henry ^a   Couturier, Cédric ^a   Monteiro, Nuno ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; ISOQUINOLINE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; HECK REACTION; MOLECULAR DYNAMICS; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 0037239486     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b211856b     Document Type: Article

References (23)

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14. 13C NMR spectra indicated that the palladium-containing compound was obtained as a single diastereomer. The stereochemistry of the newly created stereogenic center as depicted in Scheme 1 could be predicted by the reported preference for intramolecular Heck insertions to occur via eclipsed orientations of the metal-carbons and the alkene π bond (Fig. SI 1†). See M. M. Abelman, L. E. Overman and V. D. Tran, J. Am. Chem. Soc., 1990, 112, 6959.
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16. n-N palladacycle. It should be noted that in our case triflate derivatives (i.e. 3a with X = OTf) proved essentially unreactive.
17. The crystal data have been deposited in the Cambridge Crystallographic Data Center as CCDC 1267/701 (see http://www.rsc.org/suppdata/cc/b2/b211856b/ for crystallographic files in CIF or other electronic format). C. Bavoux, C.-H. Fabritius, B. Clique, N. Monteiro and G. Balme, Z. Kristallogr., 2001, 216, 633-634.
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21. 13C NMR spectra. We believe that these are conformational isomers having restricted pyramidal nitrogen inversion and further experiments will be carried out to confirm this hypothesis.
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23. We may suggest that the putative acyl palladium complex 8 undergoes β-hydrogen elimination of the acyl ligand with elimination of ketene faster than reductive elimination of the ketone. The resulting palladium hydride 9 would then undergo reductive elimination to give 7.