Palladium-catalysed hydroarylation and hydrovinylation of 3,3-dialkoxy-1-aryl-1-propynes. An approach to 3-aryl- and 3-vinylquinolines

Tetrahedron

Volumn 52, Issue 30, 1996, Pages 10225-10240

  Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Marinelli, Fabio ^b   Moro, Leonardo ^a   Pace, Paola ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030598028     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00557-1     Document Type: Article

References (37)

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16. 11 prepared through palladium-catalysed vinylic substitution reactions. Therefore, we inferred that 4 and 5 were the hydroarylation products with the added aryl unit on the carbon bearing the carbonyl group. The stereochemistry of 5 was assigned on the basis of a NOE study, which showed that the vinyl proton and the acyl group are cis (irradiation of the vinyl proton led to the enhancement of the methyl group). Compound 4, whose NOE study was prevented by the close chemical shift of the vinylic and aromatic protons, was assumed to have the vinyl proton and the carbonyl group trans.
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18. 2: C, 80.93; H, 6.39. Found: C, 80.78; H, 5.90.
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33. n in Scheme 7, it seems reasonable to suppose that under our conditions (in the absence of phosphine and other strong ligands) the active palladium(0) species are stabilised by coordination to the acetylenic π-electrons. For example, the palladium catalyst was found to precipitate very quickly as a dark powder when diphenylacetylene was slowly added to a dimethylformamide solution containing a vinyl triflate, catalytic amounts of a palladium catalyst, and potassium formate (unpublished results).
34. aSamuel, E.G.; Norton, J.R. J. Am. Chem. Soc. 1984, 106, 5505;
35. bde Vaal, P.; Dedieu, A.J. J. Organomet. Chem. 1994, 478, 121.
36. 25. Mopac 6.0 data for acetylenic carbons of 6. 9a and 9f using the Hamiltonian AM 1 of substructures with optimised bond lengths, bond angles, and torsional angles are as follows. (Equation Presented)
37. 6a,e, 7,13b