Vito Fiandanese

Iron catalyzed cross-coupling reactions of acyl chlorides with Grignard reagents. A mild, general, and convenient synthesis of aliphatic and aromatic ketones

Abstract Acyl chlorides couple with Grignard reagents at room temperature in the presence of catalytic amounts of tris(acetylacetonate)iron(III), Fe(acac) 3 . The reaction is general with respect to both reactants and provides a very mild and convenient method for the synthesis of aliphatic and aromatic ketones.

A highly efficient synthetic route to ketones through sequential coupling reactions of Grignard reagents with S-phenyl carbonochloridothioate in the presence of nickel or iron catalysts

Abstract The sequential coupling reactions of Grignard reagents with S phenyl carbonochloridothioate in the presence of nickel(II) or iron(III) catalysts provides a very mild and straightforward route to symmetrical and unsymmetrical aliphatic and aromatic ketones.

A direct access to α-diones from oxalyl chloride

Abstract Cross-coupling reactions of oxalyl chloride with organocopper reagents, derived from Grignard reagents, cuprous bromide, and lithium bromide, provide a simple and straightforward method for the synthesis of symmetrical α-diones in very good yields.

Functionalized ketones by iron mediated reaction of grignard reagents with acyl chlorides

Abstract The iron(III)-catalyzed cross-coupling reaction between Grignard reagents and acyl chlorides was found to be widely applicable to the synthesis of various functionalized ketones in good yields under mild conditions; the series of examples includes the synthesis of chiral methyl ketones and symmetric diketones.

ONE-STEP SYNTHESIS OF DIALKYNYL-1,2-DIONES AND THEIR CONVERSION TO FUSED PYRAZINES BEARING ENEDIYNE UNITS

Abstract A convenient procedure for the preparation of symmetrically end-protected dialkynyl-1,2-diones 3 from lithium acetylides and oxalyl chloride in the presence of CuBr and LiBr is described. The condensation of 3 with various aromatic and heteroaromatic 1,2-diamines leads to pyrazine-based α-dialkynylated heterocycles. The enediyne substructure of diethynylquinoxaline can be thermally rearranged in a Bergman cyclization reaction.

A straightforward route to polyenylsilanes by palladium- or nickel-catalyzed cross-coupling reactions

Abstract An efficient conversion of bis-silylated dienes and trienes into polyenylsilanes by cross-coupling reactions is described. The aryl substituted polyenes are synthesized by ipso-borodesilylation with BCl3 followed by Pd-catalyzed coupling reactions of the resulting boron derivative with aryl halides, whereas the synthesis of alkyl substituted polyenes requires the conversion of the boron intermediate into iodo-derivative and the subsequent coupling with alkyl Grignard reagents in the presence of a Ni(II) catalyst.

A new straightforward and general approach to dienamide natural products

A new synthetic approach to various conjugated (E,E) dienamides has been developed, starting from an easily accessible bifunctional dienyl compound and based upon a double selective electrophilic substitution, followed by coupling reactions.

Stereospecific synthesis of (1E,3Z)- and (1E,3E)-1-trimethylsilyl-1,3- dienes by means of sequential cross-coupling reactions

Abstract A new synthesis of stereodefined 1-trimethyl-1,3-dienes is described. The method is based on two sequential coupling reactions between Grignard and the readily available (Z)- or (E)-1-bromo-2-phenyl-thioethene, in the presence of transition metal catalysts.

A general and straightforward approach to α,ω-ketoesters

Abstract Chemoselective cross-coupling reactions of monoesters of dicarboxylic acid chlorides with organocopper reagents derived from Grignard reagents, cuprous bromide, and lithium bromide, provide a simple and straightforward method for synthesizing a variety of ketoesters.

One-step synthesis of ketones from car☐ylic acids and grignard reagents in the presence of a nickel(II)-phosphine catalyst.

Abstract A one-step synthesis of diaryl and alkyl-aryl ketones by the reaction of car☐ylic acid with Grignard reagents in the presence of NiCl2(Ph2PCH2CH2PPh2) as catalyst is described. In the nickel-catalyzed Grignard reaction the formation of alcohols is nearly completely suppressed.