Copper-Mediated Cross-Coupling of <i>H</i>-Phosphonates with Vinyliodonium Salts: A Novel Very Mild Synthesis of 2-Arylvinylphosphonates

Thielges, Sabine; Bisseret, Philippe; Eustache, Jacques

doi:10.1021/ol047516y

Cited by 106 publications

(38 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…A recent example of such a reaction is represented by the copper-mediated cross-coupling of H-phosphonates 413 with vinyliodonium salts 412 leading to 2-arylvinylphosphonates 414 under mild conditions (Scheme 137). 802…”

Section: Iodine(iii) Compoundsmentioning

confidence: 99%

Chemistry of Polyvalent Iodine

2008

View full text Add to dashboard Cite

Section: Iodine(iii) Compoundsmentioning

confidence: 99%

Chemistry of Polyvalent Iodine

2008

View full text Add to dashboard Cite

“…A palladium catalyzed transformation of an aryl bromide to an aryl phosphonate was used in a synthesis of (S)-APICA [588]. Copper catalyzed the coupling of alkenyliodonium salts with phosphonates [589].…”

Section: Carbon-tin -Silicon -Phosphorous -Arsenic -Antimony -Sementioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

View full text Add to dashboard Cite

“…11a All yields are based upon isolated material unless specified. 1 H and 13 C chemical shifts were determined by reference to residual protonated solvent resonances or Me 4 Si. All coupling constants are given in hertz.…”

Section: Methodsmentioning

confidence: 99%

Arylpalladium Phosphonate Complexes as Reactive Intermediates in Phosphorus−Carbon Bond Forming Reactions

et al. 2009

View full text Add to dashboard Cite

Phosphorus-carbon bond formation from discrete transition metal complexes have been investigated through a combination of synthetic, spectroscopic, crystallographic, and computational methods. Reactive intermediates of the type (diphosphine)Pd(aryl)(P(O)(OEt) 2 ) have been prepared, characterized, and studied as possible intermediates in metal-mediated coupling reactions. Several of the reactive intermediates were characterized crystallographically, and a discussion of the solid state structures is presented. In contrast to other carbon-heteroelement bond forming reactions, palladium complexes containing electrondonating substituents on the aromatic fragment exhibited faster rates of reductive elimination. Large bite angle diphosphine ligands induced rapid rates of elimination, while bipyridine and small bite angle diphosphine ligands resulted in much slower rates of elimination. An investigation of the effect of typical impurities on the elimination reaction was carried out. While excess diphosphine, pyridine, and acetonitrile had little effect on the observed rate, the addition of water slowed the phosphorus-carbon bond forming reaction. Coordination of water to the complex was observed spectroscopically and crystallographically. Computational studies were utilized to probe the reaction pathways for P-C bond formation via Pd catalysis.

show abstract

Copper-Mediated Cross-Coupling of H-Phosphonates with Vinyliodonium Salts: A Novel Very Mild Synthesis of 2-Arylvinylphosphonates

Abstract: We report a novel, very mild, highly stereoselective preparation of 2-arylvinylphosphonates at room temperature that involves the copper iodide-mediated cross-coupling of H-phosphonates with vinyliodonium tetrafluoroborates. [Structure: see text]

Cited by 106 publications

References 24 publications

Chemistry of Polyvalent Iodine

Chemistry of Polyvalent Iodine

Transition metals in organic synthesis: Highlights for the year 2005

Arylpalladium Phosphonate Complexes as Reactive Intermediates in Phosphorus−Carbon Bond Forming Reactions

Contact Info

Product

Resources

About