Transition metal-catalyzed process for preparing alpha-arylated

Details Transition metal-catalyzed process for preparing alpha-arylated Transition metal-catalyzed process for preparing alpha-arylated

1998-10-15

2000-05-02

McKane, Joseph

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

558371, 549 70, 549483, 568312, 568317, C07D20730, C07D30702, C07C25507, C07C30316, C07C 4537

Patent

active

060574569

ABSTRACT:
The present invention is directed to a process for preparing alpha-arylated carbonyl-containing compounds, comprising the steps of reacting a compound having at least one carbonyl group with an arylating compound in the presence of a base and a transition metal catalyst under reaction conditions effective to form an alpha-arylated carbonyl-containing compound, the transition metal catalyst comprising a Group 8 metal and at least one chelating ligand selected from the group consisting of unsaturated Group 15 heterocycles, Group 15-substituted metallocenes, Group 15-substituted alkanes, Group 15-substituted arylenes, and combinations thereof. The process of the present invention simplifies the preparation of commercially significant organic alpha-aryl carbonyl-containing compounds, particularly for use in the pharmaceutical and polymer industries.

REFERENCES:
patent: 5576460 (1996-11-01), Buchwald et al.
patent: 5847166 (1998-12-01), Buchwald et al.
Muratake, H. et al., Palladium-Catalyzed Intramolecular .alpha.-Arylation of Aliphatic Ketones, Tetrahedron Letters, vol. 38, No. 43, pp. 7581-7582, 1997.
Stille, J.K., The Palladium-Catalyzed Cross-Coupling Reactions of Organotin Reagents with Organic Electrophiles, Angew, Chem., Int. Ed. Engl., 25:508-524 (1986).
Miyaura, N. et al., Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds, Chem. Rev., 95:2457-2483 (1995).
Negishi, E., Palladium- or Nickel-Catalyzed Cross Coupling. A New Selective Method for Carbon-Carbon Bond Formation, Acc. Chem. Res., 15:340-348 (1982).
Kosugi, M. et al., Arylation and l-Alkenylation on .alpha.-Position of Ketones via Tributyltin Enolates Catalyzed by Palladium Complex, Bull. Chem. Soc. Jpn., 57:242-246 (1984).
Carfagna, C. et al., Palladium-Catalyzed Coupling Reactions of Aryl Triflates or Halides with Ketene Trimethylilyl Acetals. A New Route to Alkyl 2-Arylalkanoates, J. Org. Chem., 56:261-263 (1991).
Durandetti, M. et al., Nickel-Catalyzed Direct Electrochemical Cross-Coupling between Aryl Halides and Activated Alkyl Halides, J. Org. Chem. 61:1748-1755 (1996).
Fauvargue, J.F. et al., Catalysis Of TheArylation Of The Reformatsky Reagent By Palladium Or Nickel Complexes, Synthesis Of Aryl Acid Esters, J. Organomet. Chem., 177:273-281 (1979).
Barton, D.H.R. et al., Copper Catalyzed O-Phenylation Of Phenols And Enols By Pentavalent Organobismuth Compounds, Tet. Letters, 27:3619-3622 (1986).
Barton, D.H.R. et al., Application of Aryllead(iv) Derivatives to the Preparation of 3-Aryl-4-hydroxy-1-benzopyran-2-ones, J. Chem. Soc., Perkin Trans. 1:1365-1375 (1992).
Satoh, T. et al., Palladium-Catalyzed Regioselective Mono- and Diarylation Reactions of 2-Phenylphenols and Napthols with Aryl Halides, Communications, Angew. Chem. Int. Ed. Engl. 1997, 36, No. 16, pp. 1740-1742.

Affiliated with

Also associated with

Rating

Transition metal-catalyzed process for preparing alpha-arylated does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Transition metal-catalyzed process for preparing alpha-arylated , we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Transition metal-catalyzed process for preparing alpha-arylated will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1595019