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Volumn 70, Issue 8, 2005, Pages 3099-3107

Palladium-catalyzed synthesis of tetrahydrofurans from γ-hydroxy terminal alkenes: Scope, limitations, and stereoselectivity

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; DERIVATIVES; OLEFINS; PALLADIUM; PHASE TRANSITIONS; REACTION KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 17444400818     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050022+     Document Type: Article
Times cited : (92)

References (64)
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    • Trost has noted the formation of a tetrahydrofuran side product in the Heck arylation of an enyne bearing a secondary OH group and suggested a mechanism of intermolecular carbopalladation to account for its formation. See: Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924.
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    • note
    • Ligand abbreviations: dppe = 1,2-bis(diphenylphosphino)ethane; BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl; dppf = 1,1′-bis(diphenylphosphino)ferrocene; dppb = 1,1′- bis(diphenylphosphino)butane; xantphos = 9,9-dimethyl-4,5-bis(diphenylphosphino) xanthene; dpe-phos = bis(2-diphenylphosphinophenyl)ether. All ligands are readily available from commercial sources.
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    • note
    • Most reactions proceeded to completion in ca. 2 h as judged by GC analysis of crude reaction mixtures.
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    • 1H NMR and GC.
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    • It is likely that oxidation of the alcohol accompanies reduction of the aryl bromide. However, the aldehyde side products that would be generated in this process were not detected and are likely unstable under the reaction conditions. See ref 17.
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    • 13C NMR spectroscopy and MS. See the Supporting Information.
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    • Stereochemistry of tetrahydrofuran products was established by nOe experiments or by comparison of NMR spectra to related compounds of known configuration. See the Supporting Information for complete details.
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    • Tetrafluoroethylene undergoes selective insertion into the Pt-O bond of (dppe)Pt(Me)(OMe). See ref 28a,b.
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    • note
    • Related transformations of γ-aminoalkenes to pyrrolidines have been shown to proceed through an analogous mechanism. Experimental evidence in the pyrrolidine-forming reactions supports the idea that alkene insertion occurs into the Pd-heteroatom bond rather than the Pd-carbon bond. See ref 9a.
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    • Although we currently favor this mechanism, an alternative mechanism involving alkene insertion into the Pd-C bond followed by C-O bond-forming reductive elimination cannot be unambiguously ruled out in all instances. This mechanistic pathway would also likely proceed via a cyclic, chelated intermediate such as 32, or 35. High 1,4 asymmetric induction would be unlikely if insertion into the Pd-C bond occurred from an acyclic, unchelated intermediate. For further details, see ref 8.
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    • The insertion of alkenes into Pd-C bonds in intramolecular Heck reactions occurs through a conformation in which the alkene π-bond and the Pd-C bond are eclipsed. The analogous insertion into the Pd-O bond via an eclipsed conformation is depicted in Figures 3 and 4. See: Link, J. T. Org. React. 2002, 60, 157-534.
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    • Diastereoselectivities in related Pd(II)-catalyzed carbonylations of 1-substituted 4-penten-1-ols that proceed via a Wacker-type mechanism are typically in the range of 1-3:1. See ref 7a-d.


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