81467-93-8Relevant academic research and scientific papers
Iridium-catalysed desilylative acylation of 1-alkenylsilanes
Zaranek, Maciej,Skrodzki, Maciej,Szudkowska-Fr?tczak, Justyna,Dodot, Maciej,Kownacki, Ireneusz,Orwat, Bartosz,Pawlu?, Piotr
, p. 75 - 78 (2017)
We report the iridium-catalysed desilylative acylation of styryl and dienyl silanes by acid anhydrides to afford (E)-α,β-unsaturated ketones. The [{Ir(μ-Cl)(cod)}2] catalyst is the first non-rhodium complex successfully applied for this type of
Heck-Matsuda reaction of arenediazonium salts in water
Salabert, Jordi,Sebastián, Rosa María,Vallribera, Adelina,Cívicos, José Francisco,Nájera, Carmen
, p. 2655 - 2659 (2013/03/28)
The palladium-catalyzed arylation of alkenes with aryldiazonium salts can be carried out through an environmentally friendly protocol using neat water low palladium loadings at room temperature under base-additive- and ligand-free conditions.
Palladium-catalysed heck reactions of alk-1-en-3-ones with aryl bromides: A very simple access to (E)-1-arylalk-1-en-3-ones
Lemhadri, Mhamed,Fall, Yacoub,Doucet, Henri,Santelli, Maurice
experimental part, p. 1021 - 1035 (2009/12/02)
When appropriate reaction conditions are used, very high yields of (E)-1-arylalk-1-en-3-one derivatives can be obtained by palladium-catalysed reactions of alk-1-en-3-ones with aryl bromides. The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane in combination with [Pd(C3H5)Cl]2 was found to be a very efficient catalyst for this reaction. In general, higher reaction rates were observed with electron-poor aryl bromides, but the electron-rich aryl bromides 1-bromo-4-(dimethylamino)benzene and 4-bromoanisole also led to the arylated enones in high yields. Even with sterically very congested aryl bromides such as 9-bromoanthracene, 1-bromo-2,4,6-trimethylbenzene or 1-bromo-2,4,6-triisopropylbenzene, the expected (E)-1-arylalk-1-en-3-ones were obtained in moderate to good yields. These enones appear to be unstable under the reaction conditions, and the addition of a small amount of hydroquinone to the reaction mixture was found to be crucial, especially for the vinylation of electron-deficient aryl bromides. A variety of alk-1-en-3-ones has been employed, and better results in terms of substrate/ catalyst ratios were obtained when oct-1-en-3-one or hex-1-en-3-one was used than when but-1-en-3-one or pent-1-en-3-one was used. It should be noted that several reactions can be performed with as little as 0.1-0.001 mol% catalyst. Georg Thieme Verlag Stuttgart.
Regioselective heck vinylation of electron-rich olefins with vinyl halides: Is the neutral pathway in operation?
McConville, Matthew,Saidi, Ourida,Blacker, John,Xiao, Jianliang
experimental part, p. 2692 - 2698 (2009/08/15)
Highly regioselective vinylation of electron-rich olefins by bromo- as well as chlorostyrenes is effected by palladium catalysis with either mono- or bidentate phosphines in a molecular solvent, with no need for halide scavengers, ionic liquids, or ionic additives. The use of the hemilabile 1,3-bis(diphenylphosphino)propane monoxide (dpppO) as a ligand led to faster reactions of more challenging 2-substituted vinyl ethers and reduced Pd loadings. In contrast to the related arylation reaction, evidence suggests that the vinylation may proceed via the neutral Heck mechanism.
