68587-15-5Relevant academic research and scientific papers
Palladium/copper-catalyzed decarboxylative cross-coupling of aryl chlorides with potassium carboxylates
Goossen, Lukas J.,Zimmermann, Bettina,Knauber, Thomas
, p. 7103 - 7106 (2008)
(Chemical Equation Presented) Even non-activated aryl chlorides undergo decarboxylative cross-coupling reactions in the presence of a catalyst system generated in situ from CuI, 1,10-phenanthroline, PdI2, and di(tert-butyl)biphenylphosphane. The new catalyst is useful for both the synthesis of biaryl compounds from aromatic carboxylates and the synthesis of aryl ketones from salts of α-ketocarboxylic acids (see scheme; FG=functional group; R=aryl, alkyl).
Iridium-Catalysed Reductive Deoxygenation of Ketones with Formic Acid as Traceless Hydride Donor
Yang, Zhiheng,Zhu, Xueya,Yang, Shiyi,Cheng, Weiyan,Zhang, Xiaojian,Yang, Zhanhui
supporting information, p. 5496 - 5505 (2020/10/22)
An iridium-catalysed deoxygenation of ketones and aldehydes is achieved, with formic acid as hydride donor and water as co-solvent. At low catalyst loading, a number of 4-(N,N-disubstituted amino) aryl ketones are readily deoxygenated in excellent yields and chemoselectivity. Numerous functional groups, especially phenolic and alcoholic hydroxyls, secondary amine, carboxylic acid, and alkyl chloride, are well tolerable. Geminally dideuterated alkanes are obtained with up to 90% D incorporation, when DCO2D and D2O are used in place of their hydrogenative counterparts. The activating 4-(N,N-disubstituted amino)aryl groups have been demonstrated to undergo a variety of useful transformations. The deoxygenative deuterations have been used to prepare a deuterated drug molecule Chlorambucil-4,4-d2. (Figure presented.).
Efficient Synthesis of Diaryl Ketones by Nickel-Catalyzed Negishi Cross-Coupling of Amides by Carbon–Nitrogen Bond Cleavage at Room Temperature Accelerated by a Solvent Effect
Shi, Shicheng,Szostak, Michal
, p. 10420 - 10424 (2016/07/21)
The first Negishi cross-coupling of amides for the synthesis of versatile diaryl ketones by selective C?N bond activation under exceedingly mild conditions is reported. The cross-coupling was accomplished with bench-stable, inexpensive precatalyst [Ni(PPh3)2Cl2] that shows high functional-group tolerance and enables the synthesis of highly functionalized diaryl ketone motifs. The coupling occurred with excellent chemoselectivity favoring the ketone (cf. biaryl) products. Notably, this process represents the mildest conditions for amide N?C bond activation accomplished to date (room temperature, 10 min). Considering the versatile role of polyfunctional biaryl ketone linchpins in modern organic synthesis, availability, and excellent functional-group tolerance of organozinc reagents, this strategy provides a new platform for amide N?C bond/organozinc cross-coupling under mild conditions.
PROCESS FOR PREPARING KETONES FROM ALPHA-OXO CARBOXYLATES AND ARYL BROMIDES
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Page/Page column 3-4, (2009/09/08)
A process for preparing ketones of the general formula (III) where R is an optionally substituted carbocyclic aromatic radical having 6 to 24 carbon atoms or an optionally substituted alkyl radical or an optionally substituted heteroaromatic radical having 5 to 24 carbon atoms, andR1 is an optionally substituted carbocyclic aromatic radical having 6 to 24 carbon atoms or an optionally substituted heteroaromatic radical having 5 to 24 carbon atoms, by reacting alpha-oxo carboxylates of the general formula (I) wherein n and m is a number in the range from 1 to 6, M(m+) is a cation, and R has the meaning indicated for formula (III), with aryl bromides of the general formula (II) [in-line-formulae]R1—Br ??(II)[/in-line-formulae] where R1 has the meaning indicated for formula (III), in the presence of two transition metals or compounds thereof as catalyst, is described.
Synthesis of ketones from α-oxocarboxylates and aryl bromides by Cu/Pd-catalyzed decarboxylative cross-coupling
Goossen, Lukas J.,Rudolphi, Felix,Oppel, Christoph,Rodriguez, Nuria
, p. 3043 - 3045 (2008/12/23)
(Chemical Equation Presented) The power of two metals: A Pd/Cu catalyst system mediates the in situ formation of acyl nucleophiles by decarboxylation of readily accessible and stable salts of α-oxocarboxylic acids and their cross-coupling with aryl or heteroaryl bromides to give ketones. The reaction may be usedin the presence of many functional groups and provides good yields.
