Ar−F Reductive Elimination from Palladium(II) Revisited

In contrast with [(o-Tol3P)2Pd2(p-C6H4X)2(μ-F)2] (1; X = NO2; J. Am. Chem. Soc. 2007, 129, 1342), its nonactivated congeners (X = H, Me, and MeO) do not produce 19F NMR-detectable quantities of p-FC6H4X upon thermal decomposition in the presence of Buchwald's ligand t-Bu2P-2-C6H4C6H2(i-Pr)3-2‘,...

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Bibliographic Details
Published in:Organometallics 2007-09, Vol.26 (20), p.4997-5002
Main Authors: Grushin, Vladimir V, Marshall, William J
Format: Article
Language:English
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Summary:In contrast with [(o-Tol3P)2Pd2(p-C6H4X)2(μ-F)2] (1; X = NO2; J. Am. Chem. Soc. 2007, 129, 1342), its nonactivated congeners (X = H, Me, and MeO) do not produce 19F NMR-detectable quantities of p-FC6H4X upon thermal decomposition in the presence of Buchwald's ligand t-Bu2P-2-C6H4C6H2(i-Pr)3-2‘,4‘,6‘ (BL). These results do not support the previously asserted “net Ar−F reductive elimination”, given that for X = NO2 some quantities of p-FC6H4X might conceivably be formed from 1 via a variety of other, SNAr-type paths.
ISSN:0276-7333
1520-6041
DOI:10.1021/om700469k