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DMF has been shown to be one of the most desirable solvents for Pd-catalyzed cross-coupling reactions (Negishi, E.-i.; Owczarczyk, Z.; Swanson, D. R. Tetrahedron Lett. 1991, 32, 4456) and has been frequently used in carbonylation reactions as well.
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See the literature in ref 6.
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18
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4644270788
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note
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In MeOH as the solvent (53% yield), the rest was recovered starting material.
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Similar β-hydroxyalkylbutenolides were prepared by Hoye et al. under the Stille carbonylation conditions, see: Hoye, T. R.; Humpal, P. E.; Jiménez, J. I.; Mayer, M. J.; Tan, L.; Ye, Z. Tetrahedron Lett. 1994, 35, 7517.
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In this case, the initially formed alkenylpalladium intermediate could have been stabilized by the chelation of the carbonyl oxygen to Pd, even though it should be noted that a seven-membered chelate ring would thus be formed. This kind of stabilizing effect has been proposed by Maleczka et al. to explain the regioselectivity of Pd-mediated hydrostannations of terminal alkynes; see: Rice, B. M.; Whitehead, S. L.; Horvath, C. M.; Muchnij, J. A.; Maleczka, R. E., Jr. Synthesis 2001, 1495.
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