29478-39-5Relevant academic research and scientific papers
Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination
Wang, Mei-Ling,Xu, Hui,Li, Han-Yuan,Ma, Biao,Wang, Zhen-Yu,Wang, Xing,Dai, Hui-Xiong
, p. 2147 - 2152 (2021/04/05)
Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.
Pd-catalyzed oxidative Heck-type arylation of vinyl ketones, alkenes, and acrylates with Sb-aryl-tetrahydrodibenz[c,f][1,5]azastibocines
Murata, Yuki,Kakusawa, Naoki,Arakawa, Yukako,Hayashi, Yukako,Morinaga, Shun,Ueda, Masaaki,Hyodo, Tadashi,Matsumura, Mio,Yamaguchi, Kentaro,Kurita, Jyoji,Yasuike, Shuji
, (2020/10/18)
The Pd-catalyzed cross-coupling reactions of Sb-aryl-1,5-azastibocines with alkenes are described. The reactions of azastibocines with alkenes such as vinyl ketones, alkenes, and acrylates in the presence of 10 mol% PdCl2 at 80 °C in DMA under aerobic conditions produced Heck adducts in moderate-to-excellent yields. Single-crystal X-ray and NMR analysis revealed that the aryl donors in this reaction, the Sb-aryl-1,5-azastibocines, are hypervalent compounds that display N–Sb intramolecular non-bonding interaction. These are the first examples of Pd-catalyzed Heck-type arylations using heterocyclic hypervalent organoantimony compounds. Although the reactions proceeded efficiently with the azastibocines, they hardly progressed with trivalent and pentavalent triarylantimony reagents.
Novel antiobesity agents: Synthesis and pharmacological evaluation of analogues of Rimonabant and of LH21
Alvarado, Mario,Decara, Juan,Luque, María Jesús,Hernandez-Folgado, Laura,Gómez-Ca?as, María,Gómez-Ruiz, María,Fernández-Ruiz, Javier,Elguero, José,Jagerovic, Nadine,Serrano, Antonia,Goya, Pilar,De Fonseca, Fernando Rodríguez
, p. 1708 - 1716 (2013/05/09)
Searching for novel antiobesity agents, a series of cannabinoid LH21 and of Rimonabant-fatty acid amide analogues have been prepared. Synthesis of pyrazoles 2a-2c was achieved by a two steps simple methodology via α,β-unsaturated ketones. Carboxamides 8a-8h were obtained in good yields from esters 7a-7c by a one-pot procedure which takes place under mild conditions. New compounds have been evaluated in vivo as anorectic agents. Some of them showed interesting properties reducing food intake in rats by a mechanism which does not involve the endocannabinoid system.
Recyclable gold nanoparticle catalyst for the aerobic alcohol oxidation and C-C bond forming reaction between primary alcohols and ketones under ambient conditions
Kim, Sungjin,Bae, Sang Won,Lee, Jae Sung,Park, Jaiwook
experimental part, p. 1461 - 1466 (2009/04/11)
A recyclable gold catalyst is synthesized from readily available reagents by immobilizing gold nanoparticles in aluminum oxyhydroxide support through a simple sol-gel method. The catalyst showed the high activity even at room temperature in the aerobic oxidation of various alcohols and in the coupling reaction between primary alcohols and ketones.
Gold(III)-catalyzed direct nucleophilic substitution of propargylic alcohols
Georgy, Marie,Boucard, Valérie,Debleds, Olivier,Zotto, Christophe Dal,Campagne, Jean-Marc
experimental part, p. 1758 - 1766 (2009/06/28)
Gold-catalyzed nucleophilic substitution of propargylic alcohols with various nucleophiles (allylsilane, electron-rich aromatics, alcohols, thiols, hydrides, 1,3-dicarbonyl derivatives, sulfonamides) is described under very mild conditions (room temperatu
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.
One single catalyst, Pd(OAc)2, for two sequential very different steps: Allylic alcohol oxidation-Heck reaction. Access to functionalised α,β-unsaturated ketones
Batt, Frederic,Gozzi, Christel,Fache, Fabienne
supporting information; experimental part, p. 5830 - 5832 (2009/04/13)
A single addition of the catalyst, Pd(OAc)2, was realised to mediate two transformations as different as allylic alcohol oxidation under O2 and C-C bond formation of the Heck type, to give substituted α,β-unsaturated ketones without intermediate purification. The Royal Society of Chemistry.
Palladium-catalyzed Heck arylations of allyl alcohols in ionic liquids: Remarkable base effect on the selectivity
Calo, Vincenzo,Nacci, Angelo,Monopoli, Antonio,Ferola, Valentina
, p. 2596 - 2601 (2007/10/03)
Pd-catalyzed Heck arylation of allyl alcohols in tetraalkylammonium ionic liquids (ILs) can be made highly selective toward the formation of either aromatic carbonyl compounds or aromatic conjugated alcohols by carefully choosing both the IL and the base.
Stereoselective functionalization of β-iodo-α,β-unsaturated ketones via an iodine-copper exchange reaction
Yang, Xiaoyin,Knochel, Paul
, p. 1941 - 1943 (2007/10/03)
β-Iodo-α,β-unsaturated carbonyl compounds undergo a stereoselective iodine-copper exchange reaction with (Nphyl)2CuLi, providing the corresponding alkenyl cuprates with retention of the double bond configuration. No competitive addition/elimina
Recyclable palladium catalyst for highly selective α alkylation of ketones with alcohols
Kwon, Min Serk,Kim, Namdu,Seo, Seong Hyeok,Park, In Soo,Cheedrala, Ravi Kumar,Park, Jaiwook
, p. 6913 - 6915 (2007/10/03)
(Chemical Equation Presented) An air-stable, heterogeneous, and recyclable catalyst composed of palladium nanoparticles entrapped in aluminum hydroxide was applied to a highly selective α alkylation. A wide range of aliphatic and aromatic ketones and primary alcohols were coupled to prepare enones in an O2 atmosphere and ketones in an argon atmosphere (see scheme).
