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It is well known that beta-diketones can undergo condensations at the alpha-methylene group with alkyl halides and certain other reagents though the intermediate formation of monoanions. For example, on treatment with an alkali metal or an alkali metal alkoxide or carbonate forms a mono-anion which can be alkylated with alkyl halides. In 1958, Hauser and Harris reported that, if or is first converted to the dipotassium salt. The salt undergoes alkylation and other carbon-carbon condensations at the terminal methyl group rather than at the methylene group. Rapid alkylation was observed when the salts were treated with and after acidification, the terminal monobenzylation derivatives were obtained in good yield. Dibenzylation was not observed. In this chapter alkylations of these and other beta-ketones via dianions are surveyed. Other alkylations are also discussed. Arylations are included because alkylation and arylation are methods for directly converting beta-homologs without increasing their functionality.

M.; Yu, J-.Q. "Pd(II)-Catalyzed Olefination of sp3 C-H Bonds." J.

Chan, Qian Shao and Jin-Quan Yu
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Synthesis using beta dicarbonyl compounds - …

Jian He, Toshihiko Shigenari and Jin-Quan Yu
"Palladium(0)/PAr3-Catalyzed Intermolecular Amination of C(sp3)-H Bonds: Synthesis of b-Amino Acids"
Angew.

METHOD FOR SYNTHESIZING BETA-DICARBONYL COMPOUNDS …

Dorado, L., Montoya, M.R. & Rodriguez-Mellado, J.M. (1992) A contribution to the study of the structure–mutagenicity relationship for alpha-dicarbonyl compounds using the Ames test. ., 269, 301–306.

Cheng and Jin-Quan Yu "Ligand-Promoted Borylation of C(sp3)-H Bonds with Pd(II) Catalysts"  Angew.
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The reaction of malononitrile with some β-dicarbonyl compounds

Wasa, M.; Yu, J-.Q.
"Amide-Directed Arylation of sp3 C-H Bonds using Pd(II) and Pd(0) Catalysts."
Tetrahedron 2010, 66, 4811.

WITH SOME BETA-DICARBONYL COMPOUNDS

-F.; Yu, J.-Q.
"Key Mechanistic Features of Enantioselective C-H Bond Activation Reactions Catalyzed by [(Chiral Mono-N-Protected Amino Acid)-Pd(II)] Complexes."
J.

by the reaction of 1,3-dicarbonyl compounds with amines in the ..

Giri, R.; Yu, J.-Q.
"Synthesis of 1,2 and 1,3-dicarboxylic Acids via Pd(II)-Catalyzed Carboxylation of" Aryl and Vinyl C-H Bonds""
J.

Carbonyl Reactivity - Michigan State University

Li Wan, Navid Dastbaravardeh, Gang Li and Jin-Quan Yu
"Cross-Coupling of Remote meta-C-H Bonds Directed by a U-Shaped Template"
J.

Carboxyl Reactivity - Michigan State University

Houk
"Palladium-Catalyzed meta-Selective C-H Bond Activation with a Nitrile-Containing Template: A Computational Study on Mechanism and Origins of Selectivity"
J.

and beta-dicarbonyl compounds ..

Mei, T.-S.; Wang, X.; Yu, J.-Q.
"Pd(II)-catalyzed Amination of C-H Bonds Using Single-electron or Two-electron Oxidants"
J.