52513-06-1Relevant articles and documents
The first synthesis of threo- and erythro-(E)-4,5-dihydroxydec-2-enals carbonyls related to the peroxidation of liver microsomal lipids
Allevi, Pietro,Cajone, Francesco,Ciuffreda, Pierangela,Anastasia, Mario
, p. 1347 - 1350 (1995)
The first synthesis of threo and erythro (E)-4,5-dihydroxydec-2-enals, aldehydes related to the lipid peroxidation is accomplished by reaction of α-benzoyloxheptanal with the Grignard reagent of 3,3-diethoxy-1-propyne and lithium aluminium hydride reducti
Catalyst Deactivation During Rhodium Complex-Catalyzed Propargylic C?H Activation
M?ller, Saskia,Jannsen, Nora,Rüger, Julia,Drexler, Hans-Joachim,Horstmann, Moritz,Bauer, Felix,Breit, Bernhard,Heller, Detlef
supporting information, p. 14034 - 14041 (2021/08/06)
Detailed mechanistic investigations on our previously reported synthesis of branched allylic esters by the rhodium complex-catalyzed propargylic C?H activation have been carried out. Based on initial mechanistic studies, we present herein more detailed investigations of the reaction mechanism. For this, various analytical (NMR, X-ray crystal structure analysis, Raman) and kinetic methods were used to characterize the formation of intermediates under the reaction conditions. The knowledge obtained by this was used to further optimize the previous conditions and generate a more active catalytic system.
Copper-catalyzed regioselective allylic oxidation of olefins via C–H activation
Zhu, Nengbo,Qian, Bo,Xiong, Haigen,Bao, Hongli
supporting information, p. 4125 - 4128 (2017/09/29)
A regioselective oxidation of allylic C–H bond to C–O bond catalyzed by copper (I) was developed with diacyl peroxides as oxidants. The oxidation of allylic C–H bond was accomplished with good yield and regioselectivity under mild reaction conditions. This method has a broad substrate scope including cyclic olefins, terminal and internal acyclic olefins and allyl benzene compounds. The reaction proceeds by a radical mechanism as suggested by spin trapping experiments.
Regioselective Asymmetric Allylic Alkylation Reaction of α -Cyanoacetates Catalyzed by a Heterobimetallic Platina-/Palladacycle
Weiss, Marcel,Holz, Julia,Peters, Ren
, p. 210 - 227 (2016/01/20)
Allylic substitution reactions provide a valuable tool for the functionalization of CH acidic pronucleophiles. Often, control over the stereocenter generated at the nucleophilic reactant is still a challenge. The majority of studies that address this issue employ metal complexes with a low metal oxidation state (e.g. Pd0) to form allyl complexes through oxidative addition. In this article we describe the use of heterobimetallic PtII/PdII complexes, which probably activate the olefinic substrates through an SN2′ pathway. The reaction of α-cyanoacetates delivers linear allylation products with exclusive regioselectivity and high E/Z-selectivity for the new C=C double bond. Although the enantioselectivities attained are moderate, they are significantly higher than with related mono-PdII or -PtII catalysts or the corresponding bis-PdII complex, which indicates cooperation of the different metals. Control experiments suggest simultaneous activation of both reaction partners.
Mechanistic investigations of the rhodium catalyzed propargylic CH activation
Gellrich, Urs,Meissner, Antje,Steffani, Alberto,Kaehny, Matthias,Drexler, Hans-Joachim,Heller, Detlef,Plattner, Dietmar A.,Breit, Bernhard
supporting information, p. 1097 - 1104 (2014/02/14)
Previously we reported the redox-neutral atom economic rhodium catalyzed coupling of terminal alkynes with carboxylic acids using the DPEphos ligand. We herein present a thorough mechanistic investigation applying various spectroscopic and spectrometric m
Redox-neutral atom-economic rhodium-catalyzed coupling of terminal alkynes with carboxylic acids toward branched allylic esters
Lumbroso, Alexandre,Koschker, Philipp,Vautravers, Nicolas R.,Breit, Bernhard
supporting information; experimental part, p. 2386 - 2389 (2011/05/04)
A new method for the preparation of a wide range of branched allylic esters from terminal alkynes that proceeds via a redox-neutral propargylic CH activation employing a rhodium(I)/DPEphos catalyst is reported.
Copper catalyzed asymmetric synthesis of chiral allylic esters
Geurts, Koen,Fletcher, Stephen P.,Feringa, Ben L.
, p. 15572 - 15573 (2007/10/03)
The complex derived from Taniaphos ligand 4 and CuBr?Me2S catalyzes the asymmetric addition of Grignard reagents to 3-bromopropenyl esters 1 to provide allylic esters 2 in high yields and high chemio-, regio-, and enantioselectivities. The work demonstrates that allylic asymmetric alkylation (AAA) can be done on substrates bearing a heteroatom at the γ-position. The method is a practical route to chiral, nonracemic allylic alcohols. The use of functionalized substrates 1 or Grignard reagents leads to more complex products 2, which can be further manipulated as demonstrated in conversion to (S)-5-ethyl-2(5H)-furanone 6 and (S)-benzoic acid-cyclopent-2-enyl ester 7. Copyright
Water-soluble and reusable copper catalyst for the allylic benzoyloxylation of olefins
Le Bras, Jean,Muzart, Jacques
, p. 431 - 433 (2007/10/03)
Simple mixing of [(HOCH2CH2NHCOCH2)2NCH 2]2 with Cu(MeCN)4BF4 in water led to an efficient and reusable catalytic system for the allylic oxidation of olefins by tert-b
Allylic oxidation of olefins in the presence of Cu-Na-HSZ-320 zeolite as reusable solid catalyst
Carloni,Frullanti,Maggi,Mazzacani,Bigi,Sartori
, p. 8947 - 8950 (2007/10/03)
The Cu-Na-HSZ-320 zeolite can be utilised as an efficient and reusable catalyst in the allylic oxidation of olefins with tert-butyl perbenzoate to give the corresponding allylic esters in good yield and excellent selectivity. (C) 2000 Elsevier Science Ltd
Cu(OTf)2-DBN/DBU complex as an efficient catalyst for allylic oxidation of olefins with tert-butyl perbenzoate
Sekar, Govindasamy,DattaGupta, Arpita,Singh, Vinod K.
, p. 8435 - 8436 (2007/10/03)
Olefins, on treatment with tert-butyl perbenzoate in the presence of a catalytic amount of a complex of Cu(OTf)2 and chelating ligands such as DBN and DBU gave allylic benzoates under milder conditions. A variety of olefins were tested in the reaction.
