13757-90-9Relevant academic research and scientific papers
Stoichiometric reactions of acylnickel(II) complexes with electrophiles and the catalytic synthesis of ketones
Wotal, Alexander C.,Ribson, Ryan D.,Weix, Daniel J.
supporting information, p. 5874 - 5881 (2015/01/09)
Acylnickel(II) complexes feature prominently in cross-electrophile coupling (XEC) reactions that form ketones, yet their reactivity has not been systematically investigated. We present here our studies on the reactivity of acylnickel(II) complexes with a series of carbon electrophiles. Bromobenzene, α-chloroethylbenzene, bromooctane, and iodooctane were reacted with (dtbbpy)NiII(C(O)C5H11)(Br) (1b) and (dtbbpy)NiII(C(O)tolyl)(Br) (1c) to form a variety of organic products. While reactions with bromobenzene formed complex mixtures of ketones, reactions with α-chloroethylbenzene were highly selective for the cross-ketone product. Reactions with iodooctane and bromooctane also produced the cross-ketone product, but in intermediate yield and selectivity. In most cases the presence or absence of a chemical reductant (zinc) had only a small effect on the selectivity of the reaction. The coupling of 1c with iodooctane (60% yield) was translated into a catalytic reaction, the carbonylative coupling of bromoarenes with primary bromoalkanes (six examples, 60% average yield).
Oxidation of alcohols with nitroxyl radical under polymer-supported two-phase conditions
Yoshitomo, Kashiwagi,Chiba, Shinya,Anzai, Jun-ichi
, p. 1545 - 1549 (2007/10/03)
The oxidation of alcohols to carbonyl compounds was studied using potassium hexacyanoferrate(III) mediated by nitroxyl radical as the catalyst under polymer-supported organic-aqueous two-phase conditions. Primary alcohols are readily oxidized to the corresponding aldehydes in excellent yield with no over-oxidation to carboxylic acids. Secondary alcohols are converted to the corresponding ketones with a much lower efficiency. The oxidation reactions of primary alcohols in the presence of secondary alcohols is strongly favored. Primary-secondary diols are selectively transformed into hydroxy aldehydes with small amounts of ketoaldehydes, the amount of isomeric keto alcohols remaining is less than 1%.
Cobalt(II) Chloride Catalysed Coupling of Acetic Anhydride with Aldehydes. A Novel Synthesis of Asymmetrical 1,2-Diones
Ahmad, Saeed,Iqbal, Javed
, p. 692 - 693 (2007/10/02)
Cobalt(II) chloride in acetonitrile efficiently catalyses the coupling of acetic anhydride with various aldehydes to the corresponding 1,2-diones in very high yields.
REDUCTIVE COUPLING OF S-(2-PYRIDYL) ALIPHATIC THIOATES BY USE OF BIS(1,5-CYCLOOCTADIENE)NICKEL
Onaka, Makoto,Matsuoka, Yoshio,Mukaiyama, Teruaki
, p. 905 - 906 (2007/10/02)
S-(2-Pyridyl) aliphatic thioates are reductively dimerized to give α-diketones and α-hydroxy ketones on treatment with bis(1,5-cyclooctadiene)nickel at 40 deg C.
