- Formation of pyrrolidines by the titanocene(II)-promoted intramolecular reaction of N-[3,3-bis(phenylthio)propyl]anilides
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The reaction of anilides with the titanium carbene complexes generated by the desulfurization of thioacetals with the titanocene(II) species Cp2Ti[P(OEt)3]2 produced the corresponding enamines. Unusual formation of pyrroli
- Takeda, Takeshi,Saito, Jun,Tsubouchi, Akira
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Read Online
- Neutral-eosin Y-catalyzed regioselective hydroacylation of aryl alkenes under visible-light irradiation
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Styrene derivatives were hydroacylated with exclusive anti-Markovnikov selectivity by using neutral eosin Y as a direct hydrogen-atom-transfer (HAT) catalyst under visible-light irradiation. Aldehydes and styrenes with various substituents were tolerated (>20 examples), giving the corresponding products in moderate to high yields. The key acyl radical intermediate was generated from a direct HAT process induced by photoexcited eosin Y. Subsequent addition to styrenes and a reverse HAT process generated the ketone products.
- Liu, Haiwang,Xue, Fei,Wang, Mu,Tang, Xinxin,Wu, Jie
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supporting information
p. 406 - 410
(2020/12/30)
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- Palladium Catalysis for Aerobic Oxidation Systems Using Robust Metal–Organic Framework
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Described here is a new and viable approach to achieve Pd catalysis for aerobic oxidation systems (AOSs) by circumventing problems associated with both the oxidation and the catalysis through an all-in-one strategy, employing a robust metal–organic framework (MOF). The rational assembly of a PdII catalyst, phenanthroline ligand, and CuII species (electron-transfer mediator) into a MOF facilitates the fast regeneration of the PdII active species, through an enhanced electron transfer from in situ generated Pd0 to CuII, and then CuI to O2, trapped in the framework, thus leading to a 10 times higher turnover number than that of the homogeneous counterpart for Pd-catalyzed desulfitative oxidative coupling reactions. Moreover, the MOF catalyst can be reused five times without losing activity. This work provides the first exploration of using a MOF as a promising platform for the development of Pd catalysis for AOSs with high efficiency, low catalyst loading, and reusability.
- Li, Jiawei,Liao, Jianhua,Ren, Yanwei,Liu, Chi,Yue, Chenglong,Lu, Jiaming,Jiang, Huanfeng
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supporting information
p. 17148 - 17152
(2019/11/03)
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- Two efficient pathways for the synthesis of aryl ketones catalyzed by phosphorus-free palladium catalysts
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Allylic alcohols, 1-buten-3-ol, 1-penten-3-ol and 1-octen-3-ol, reacted with aryl iodides (iodotoluene, 4-iodotoluene, 4-iodophenol and 4-iodanisole) under Heck reaction conditions to form corresponding saturated aryl ketones in one step. The same products were obtained in a two-step tandem reaction consisted of the Heck coupling of allylic alcohols with aryl iodides, followed by hydrogenation. Reactions were catalyzed by phosphorus-free palladium precursors modified with the menthol-substituted imidazolium chlorides. Formation of crystalline palladium nanoparticles, of the diameter up to 65 nm, in the reaction mixture was evidenced by TEM.
- Wirwis,Feder-Kubis,Trzeciak
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- NNN pincer Ru(II)-complex-catalyzed α-alkylation of ketones with alcohols
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A series of novel ruthenium(II) complexes supported by a symmetrical NNN ligand were prepared and fully characterized. These complexes exhibited good performance in transfer hydrogenation to form new C-C bonds using alcohols as the alkylating agents, generating water as the only byproduct. A broad range of substrates, including (hetero)aryl- or alkyl-ketones and alcohols, were well tolerated under the optimized conditions. Notably, α-substituted methylene ketones were also investigated, which afforded α-branched steric hindrance products. A potential application of α-alkylation of methylene acetone to synthesize donepezil was demonstrated, which provided the desired product in 83% yield. Finally, this catalytic system could be applied to a one-pot double alkylation procedure with sequential addition of two different alcohols. The current protocol is featured with several characteristics, including a broad substrate scope, low catalyst (0.50 mol %) loadings, and environmental benignity.
- Cao, Xiao-Niu,Wan, Xiao-Min,Yang, Fa-Liu,Li, Ke,Hao, Xin-Qi,Shao, Tian,Zhu, Xinju,Song, Mao-Ping
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p. 3657 - 3668
(2018/04/14)
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- Tandem Cross Coupling Reaction of Alcohols for Sustainable Synthesis of β-Alkylated Secondary Alcohols and Flavan Derivatives
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A Ru(II) NHC complex (loading down to 0.001 mol%) catalyzed cross coupling of a broad range of aromatic, aliphatic and heterocyclic alcohols is reported. This protocol also functioned efficiently under solvent-free conditions. Remarkably, this catalytic system disclosed so far the highest TON of 288000 for the cross coupling of alcohols. Notably, this methodology was successfully applied for the one-pot synthesis of a range of flavan derivatives. A detailed DFT studies and kinetic experiments were performed to understand the reaction mechanism as well as the high reactivity of this catalytic system. (Figure presented.).
- Shee, Sujan,Paul, Bhaskar,Panja, Dibyajyoti,Roy, Bivas Chandra,Chakrabarti, Kaushik,Ganguli, Kasturi,Das, Ayan,Das, Gourab Kanti,Kundu, Sabuj
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supporting information
p. 3888 - 3893
(2017/10/07)
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- Cobalt-Catalyzed α-Alkylation of Ketones with Primary Alcohols
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An ionic cobalt-PNP complex is developed for the efficient α-alkylation of ketones with primary alcohols for the first time. A broad range of ketone and alcohol substrates were employed, leading to the isolation of alkylated ketones with yields up to 98%. The method was successfully applied to the greener synthesis of quinoline derivatives while using 2-aminobenzyl alcohol as an alkylating reagent.
- Zhang, Guoqi,Wu, Jing,Zeng, Haisu,Zhang, Shu,Yin, Zhiwei,Zheng, Shengping
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supporting information
p. 1080 - 1083
(2017/03/14)
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- Bifunctional Ru(II) complex catalysed carbon-carbon bond formation: an eco-friendly hydrogen borrowing strategy
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The atom economical borrowing hydrogen methodology enables the use of alcohols as alkylating agents for selective C-C bond formation. A bifunctional 2-(2-pyridyl-2-ol)-1,10-phenanthroline (phenpy-OH) based Ru(ii) complex (2) was found to be a highly efficient catalyst for the one-pot β-alkylation of secondary alcohols with primary alcohols and double alkylation of cyclopentanol with different primary alcohols. Exploiting the metal-ligand cooperativity in complex 2, several aromatic, aliphatic and heteroatom substituted alcohols were selectively cross-coupled in high yields using significantly low catalyst loading (0.1 mol%). An outer-sphere mechanism is proposed for this system as exogenous PPh3 has no significant effect on the rate of the reaction. Notably, this is a rare one-pot strategy for β-alkylation of secondary alcohols using a bifunctional Ru(ii)-complex. Moreover, this atom-economical methodology displayed the highest cumulative turn over frequency (TOF) among all the reported transition metal complexes in cross coupling of alcohols.
- Chakrabarti, Kaushik,Paul, Bhaskar,Maji, Milan,Roy, Bivas Chandra,Shee, Sujan,Kundu, Sabuj
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p. 10988 - 10997
(2016/12/06)
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- An efficient heterogenized palladium catalyst for N-alkylation of amines and α-alkylation of ketones using alcohols
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A silica supported palladium-NiXantphos complex is reported as an efficient and a high turnover heterogeneous catalyst for the N-alkylation of amines and the α-alkylation of ketones using readily available alcohols under neat conditions at 120-140 °C following hydrogen borrowing strategy. The catalyst is easily separable and offers negligible amount of palladium leaching (0.01 ppm). A high turnover number of about 46000 for the N-alkylation of amines and 4400 for the α-alkylation of ketones were achieved in the respective single batch reactions. The catalyst is recyclable up to four times without appreciable change in catalytic performance.
- Dang, Tuan Thanh,Shan, Siah Pei,Ramalingam, Balamurugan,Seayad, Abdul Majeed
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p. 42399 - 42406
(2015/05/20)
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- Oxidation and β-Alkylation of Alcohols Catalysed by Iridium(I) Complexes with Functionalised N-Heterocyclic Carbene Ligands
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The borrowing hydrogen methodology allows for the use of alcohols as alkylating agents for C-C bond forming processes offering significant environmental benefits over traditional approaches. Iridium(I)-cyclooctadiene complexes having a NHC ligand with a O- or N-functionalised wingtip efficiently catalysed the oxidation and β-alkylation of secondary alcohols with primary alcohols in the presence of a base. The cationic complex [Ir(NCCH3)(cod)(MeIm(2- methoxybenzyl))][BF4] (cod=1,5-cyclooctadiene, MeIm=1-methylimidazolyl) having a rigid O-functionalised wingtip, shows the best catalyst performance in the dehydrogenation of benzyl alcohol in acetone, with an initial turnover frequency (TOF0) of 1283 h-1, and also in the β-alkylation of 2-propanol with butan-1-ol, which gives a conversion of 94 % in 10 h with a selectivity of 99 % for heptan-2-ol. We have investigated the full reaction mechanism including the dehydrogenation, the cross-aldol condensation and the hydrogenation step by DFT calculations. Interestingly, these studies revealed the participation of the iridium catalyst in the key step leading to the formation of the new C-C bond that involves the reaction of an O-bound enolate generated in the basic medium with the electrophilic aldehyde.
- Jiménez, M. Victoria,Fernández-Tornos, Javier,Modrego, F. Javier,Pérez-Torrente, Jesús J.,Oro, Luis A.
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p. 17877 - 17889
(2015/12/08)
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- Palladium-Catalyzed Desulfitative Oxidative Coupling between Arenesulfinic Acid Salts and Allylic Alcohols: A Strategy for the Selective Construction of β-Aryl Ketones and Aldehydes
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An efficient palladium-catalyzed desulfitative oxidative coupling of sodium arylsulfinites for highly region-selective Heck-type reaction of allylic alcohols has been developed. The compatibility of the functionalities of -I, -Br, and -F would explore further postfunctionalization of the C-X bonds. This method provides a new and straightforward protocol for the synthesis of β-aryl ketones and aldehydes. The deuterium labeling experiments indicated that this transformation may proceed via a [1, 2-H] shift process.
- Liao, Jianhua,Zhang, Zhenming,Tang, Xiaodong,Wu, Wanqing,Guo, Wei,Jiang, Huanfeng
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p. 8903 - 8909
(2015/09/15)
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- Replacing a stoichiometric silver oxidant with air: Ligated Pd(II)-catalysis to β-aryl carbonyl derivatives with improved chemoselectivity
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Air was employed as a green reoxidant of Pd(0), replacing stoichiometric and toxic silver salt, in the chelation-controlled Pd(II)-modulated arylative enolization of prop-2-en-1-ols to acquire synthetically-important β-aryl carbonyl derivatives. This green approach, which didn't require acid or base, allowed the compatibility of a range of functionalities (inclusive of -I, -Br & -Cl), resulting in the construction of structurally-diverse dihydrochalcones, α-benzyl-α′-alkyl acetones, α-benzyl β-keto esters and dihydrocinnamaldehydes. In addition to organoboronic acids, efficient coupling was also achieved with boronic esters and trifluoroborate salts. A deuterium labelling experiment revealed an interesting 1,2-hydrogen shift after β-arylation in the catalytic process. the Partner Organisations 2014.
- Vellakkaran, Mari,Andappan, Murugaiah M.S.,Kommu, Nagaiah
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supporting information
p. 2788 - 2797
(2014/05/06)
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- Ligated regioselective PdII catalysis to access β-aryl-bearing aldehydes, ketones, and β-keto esters
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By employing ligands in the PdII-mediated arylative isomerization of allyl alcohols, a milder and regioselective access to the versatile building blocks β-aryl aldehydes and ketones was developed. This new and chelation-controlled protocol enabled the compatibility of wide range of functionalities to generate dihydrochalcones, α-benzyl-α′- alkyl acetones, dihydrocinnamaldehydes, and α-benzyl β-keto esters (from Baylis-Hillman adducts). A practical multigram synthesis of an intermediate for Propafenone was also demonstrated. Copyright
- Vellakkaran, Mari,Andappan, Murugaiah M. S.,Kommu, Nagaiah
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supporting information; experimental part
p. 4694 - 4698
(2012/09/22)
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- C-X (X=Br, I) bond-tolerant aerobic oxidative cross-coupling: A strategy to selectively construct β-aryl ketones and aldehydes
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Using moelcular oxygen as the terminal oxidant, various aryl halide-containing β-aryl ketones and aldehydes can be synthesized directly from readily available allyic alcohols and boronic acids via palladium-catalyzed oxidative cross-coupling reactions. The dual roles of copper, including electron-carrier and Lewis acid functions, are supposed to be critical for the high reactivity and selectivity of this aerobic oxidative coupling transformation. Copyright
- Chen, Mao,Wang, Jie,Chai, Ziyi,You, Cai,Lei, Aiwen
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supporting information; experimental part
p. 341 - 346
(2012/05/04)
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- An Efficient α-alkylation of aromatic ketones with primary alcohols catalyzed by [cp*ircl2]2 without solvent
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Aromatic ketones are directly alkylated at α position with primary alcohols at 110°C in the presence of catalytic amount of KOH and [Cp*IrCl2]2 (Cp=pentamethylcyclopentadienyl) catalyst. The reaction is carried out in the absence of any solvent or additive, which generates only water as the byproduct in theory. It is very efficient and generally completed in 10 min in good isolated yields. The reaction is believed to undergo successive hydrogen transfer and cross aldol condensation processes. Copyright
- Li, Jian,Zhang, Weixing,Wang, Feng,Jiang, Min,Dong, Xiaochun,Zhao, Weili
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p. 2363 - 2366,4
(2020/09/16)
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- Operationally simple and highly (E)-styrenyl-selective heck reactions of electronically nonbiased olefins
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Simple, mild, and efficient conditions are reported for a Pd 0-catalyzed Heck reaction that delivers high yields and selectivity for (E)-styrenyl products using electronically nonbiased olefin substrates bearing a range of useful functionality. Preliminary mechanistic studies demonstrate that the σ-donating DMA solvent is crucial for high selectivity. Further studies suggest that the catalyst distinguishes between β-hydrogens on the basis of their relative hydridic character, in contrast to previously reported PdII-catalyzed oxidative reaction conditions.
- Werner, Erik W.,Sigman, Matthew S.
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supporting information; experimental part
p. 9692 - 9695
(2011/08/06)
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- Alcohols for the α-alkylation of methyl ketones and indirect aza-wittig reaction promoted by nickel nanoparticles
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Nickel nanoparticles have been found to activate primary alcohols used for the α-alkylation of ketones or in indirect aza-Wittig reactions. These processes involve hydrogen transfer from the alcohol to the intermediate α,β-unsaturated ketone or imine, respectively. All these reactions are carried out in the absence of any ligand, hydrogen acceptor or base under mild reaction conditions. For the first time nickel is employed as a potential alternative to noble-metal-based catalysts in both reactions. A reaction mechanism is proposed on the basis of some deuteration experiments. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Alonso, Francisco,Riente, Paola,Yus, Miguel
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experimental part
p. 4908 - 4914
(2009/05/27)
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- Palladium-catalyzed Heck arylations of allyl alcohols in ionic liquids: Remarkable base effect on the selectivity
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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.
- Calo, Vincenzo,Nacci, Angelo,Monopoli, Antonio,Ferola, Valentina
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p. 2596 - 2601
(2007/10/03)
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- The α-alkylation of methyl ketones with primary alcohols promoted by nickel nanoparticles under mild and ligandless conditions
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Nickel nanoparticles have been found to promote the α-alkylation of ketones with primary alcohols in the absence of any added ligand or base, under mild reaction conditions. Georg Thieme Verlag Stuttgart.
- Alonso, Francisco,Riente, Paola,Yus, Miguel
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p. 1877 - 1880
(2008/02/10)
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- Arenediazonium o-benzenedisulfonimides in Heck-type arylation of allylic alcohols
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Arenediazonium o-benzenedisulfonimides were reacted with primary and secondary allylic alcohols. The reactions, carried out in aqueous ethanol in the presence of palladium(II) acetate as precatalyst and sodium hydrogen carbonate as base, gave the arylation products with good overall conversion. In all cases, the major products were the β-arylated carbonyl derivatives. The o-benzene-disulfonimide was recovered in high yield from all the reactions, and it was recycled for the preparation of other salts. Georg Thieme Verlag Stuttgart.
- Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
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p. 3443 - 3452
(2008/02/12)
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- Easy α-alkylation of ketones with alcohols through a hydrogen autotransfer process catalyzed by RuCl2(DMSO)4
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The electrophilic α-alkylation of ketones with alcohols is accomplished by a hydrogen autotransfer process catalyzed by RuCl2(DMSO)4. The reaction can produce either simple alkylated ketones or α,β-unsaturated ketones just by choosing the appropriate starting ketones (methyl ketones or bicyclic methylenic ketones, respectively), as well as quinolines (by using 2-aminobenzyl alcohol derivatives) or the corresponding alcohol derivatives by the addition of an extra equivalent of the initial alcohol. In the last case, after the above alkylation process reduction of the carbonyl compound takes place. A mechanistic study seems to indicate that the process goes through the oxidation of the alcohols with ruthenium (after a previous deprotonation) to yield the corresponding aldehyde and a ruthenium hydride intermediate. In turn, the aldehyde suffers a classical aldol reaction with the starting ketone to form the corresponding α,β-unsaturated ketone, which finally is reduced through a Michael-type addition by the aforementioned ruthenium hydride intermediate.
- Martínez, Ricardo,Ramón, Diego J.,Yus, Miguel
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p. 8988 - 9001
(2007/10/03)
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- Ruthenium-catalyzed isomerization of alkenol into alkanone in water under irradiation of microwaves
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Ruthenium catalyzed isomerization of alkenol into alkanone through a migration of C-C double bond was performed in water under irradiation of microwaves. When the reaction was performed in deuterium oxide instead of water, the trail of the migration was shown by H-D exchange reaction. Copyright
- Ishibashi, Kenichi,Takahashi, Masaaki,Yokota, Yutaka,Oshima, Koichiro,Matsubara, Seijiro
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p. 664 - 665
(2007/10/03)
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- Recyclable palladium catalyst for highly selective α alkylation of ketones with alcohols
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(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).
- Kwon, Min Serk,Kim, Namdu,Seo, Seong Hyeok,Park, In Soo,Cheedrala, Ravi Kumar,Park, Jaiwook
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p. 6913 - 6915
(2007/10/03)
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- Solid-phase, multicomponent reactions of methyleneaziridines: Synthesis of 1,3-disubstituted propanones
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(Chemical Equation Presented) Polymer-supported methyleneaziridines undergo ring opening by Grignard reagents under copper catalysis to yield metalloenamines which are alkylated in situ to yield ketimines. Filtration and washing of these Merrifield resin-bound intermediates prior to hydrolysis provides the corresponding 1,3-disubstituted propanones in a high state of purity without recourse to column chromatography.
- Margathe, Jean-Francois,Shipman, Michael,Smith, Stephen C.
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p. 4987 - 4990
(2007/10/03)
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- An Efficient Direct α-Alkylation of Ketones with Primary Alcohols Catalyzed by [Ir(cod)CI]2/PPh3/KOH System without Solvent
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α-Alkylation of ketones was successfully achieved by the reaction of ketones with alcohols catalyzed by iridium complexes in the presence of a small amount of base. For example, 2-octanone was allowed to react with butanol under the influence of [Ir(cod)Cl]2/PPh3/KOH to give 6-dodecanone in good yield. The reaction was found to proceed by using a 1:1 mixture of ketone and alcohol without use of any solvent. Copyright
- Taguchi, Kazuhiko,Nakagawa, Hideto,Hirabayashi, Tomotaka,Sakaguchi, Satoshi,Ishii, Yasutaka
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- Arylation of allylic alcohols in ionic liquids catalysed by a Pd-benzothiazole carbene complex
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The reaction of aryl bromides with allylic alcohols catalysed by a Pd-benzothiazole carbene complex, in tetrabutylammonium bromide as solvent, leads principally to β-arylated carbonyl compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Calo, Vincenzo,Nacci, Angelo,Monopoli, Antonio,Spinelli, Michele
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p. 1382 - 1385
(2007/10/03)
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- Multicomponent reactions involving 2-methyleneaziridines: Rapid synthesis of 1,3-disubstituted propanones
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Ring opening of 1-alkyl-2-methyleneaziridines 1 or 2 is accomplished with organocopper reagents (R2CuLi or RMgX/CuI) in the presence of boron trifluoride diethyl etherate giving 1-substituted propan-2-ones 3-9 in 42-88% yield. Ring opening with RMgC1/CuI in the absence of the Lewis acid allows further alkylation of the metalloenamine (metalated imine) intermediate in a regiocontrolled manner. The sequential formation of two new intermolecular carbon-carbon bonds in this reaction provides a rapid entry into a variety of 1,3-disubstituted propan-2-ones, including 11 and 14-23. The scope and mechanism of this multicomponent reaction (MCR) has been assessed. It is established that this MCR tolerates alkyl, aryl, and benzyiic Grignard reagents and a wide range of electrophiles, including alkyl iodides, bromides, and tosylates, as well as epoxides and aldehydes. In addition, gem-dimethyl substitution on the exocyclic double bond of the 2-methyleneaziridine is tolerated. This MCR has been applied to the one-pot synthesis of (Z)-6-heneicosen11-one, 25, an important sex attractant of the Tussock moth. Using 3-deuterio-1-(1-phenylethyl)2-methyleneaziridine, 26, we determined that this MCR occurs predominantly by direct ring opening at the sp3-hybridized aziridine carbon atom (C-3).
- Hayes, Jerome F.,Shipman, Michael,Twin, Heather
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p. 935 - 942
(2007/10/03)
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- Efficient isomerization of allylic alcohols to saturated carbonyl compounds by activated rhodium and ruthenium complexes
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A range of readily available rhodium complexes of the general structures Rh(PPh3)3+ PF6- and RhX(PPh3)3 (X = H, Me, Ph) have been prepared and used in situ for the isomerization of allylic alcohols to their corresponding saturated carbonyl compounds. The isomerization of octen-3-ol, selected as a model, yielded octan-3-one in good yield. This reaction has been extended to the corresponding ruthenium complexes of the general structures [RuCl(PPh3)3]+ PF6-, RuXCl(PPh3)3 and RuX2(PPh3)3 (X = H, Me, Ph). It is noteworthy that many of these complexes have not been employed previously for this isomerization. The scope and efficiency of the process has been demonstrated by four representative complexes [RhH(PPh3)3, RuH2(PPh3)3, RuPh2(PPh3)3, RuCl(PPh3)3+ PF6-] with a wide variety of allylic alcohols. The reaction of primary allylic alcohols in the presence of RuCl(PPh3)3+ PF6- in methanol yields aldehydes protected as their methyl acetals. Deuterium labelling experiments are in agreement with a 1,3-hydride shift mechanism.
- Uma, Ramalinga,Davies, Maxwell K.,Crevisy, Christophe,Gree, Rene
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p. 3141 - 3146
(2007/10/03)
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- From allylic alcohols to saturated carbonyls using Fe(CO)5 as catalyst: Scope and limitation studies and preparation of two perfume components
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The direct conversion of allylic alcohols to saturated carbonyls, using Fe(CO)5 as a catalyst, offers good synthetic potential. Mono-, di- and even trisubstituted alkenes bearing various alkyl, aryl and electronwithdrawing groups on the allylic system give good to excellent yields of rearranged products. Limitations occur mainly with polyunsaturated derivatives. This reaction was applied to a short and efficient synthesis of cyclamen aldehyde and foliaver.
- Cherkaoui, Hassan,Soufiaoui, Mohammed,Grée, René
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p. 2379 - 2383
(2007/10/03)
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- C-H and C-C bond activation of primary amines through dehydrogenation and transimination
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Matrix presented Dehydrogenation and subsequent transimination of primary amines offer a new pathway for C-H bond activation, ortho-alkylation, and C-C bond activation to afford a variety of ketones in the reaction of 1-alkene by a cocatalyt system of Rh(I) and 2-amino-3-picoline.
- Jun, Chul-Ho,Chung, Kwan-Yong,Hong, Jun-Bae
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p. 785 - 787
(2007/10/03)
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- Generation of metalloenamines by carbon-carbon bond formation: Ring opening reactions of 2-methyleneaziridines with organometallic reagents
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Ring opening of 2-methyleneaziridines with Grignard reagents in the presence of CuI yields metalloenamines in a regiospecific fashion which can be further reacted with electrophiles to produce functionalised ketones via a one-pot process.
- Hayes,Shipman,Twin
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p. 1791 - 1792
(2007/10/03)
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- Experimental and theoretical studies on the reactivities of partially and fully fluorinated primary alkyl radicals
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Absolute rate constants for hydrogen abstraction from n-Bu3SnH by a number of partially-fluorinated and fully fluorinated n-alkyl radicals have been measured. The C-H and C-C bond dissociation energies for a number of pertinent hydrofluorocarbons have been calculated by DFT. The rate data are compared with those for addition of the same radicals to styrene, and the reactivities of these radicals are discussed in terms of their electronegativies, their structure and the thermodynamics of their reactions.
- Bartberger, Michael D.,Dolbier Jr., William R.,Lusztyk,Ingold
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p. 9857 - 9880
(2007/10/03)
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- SIMPLE AND CHEMOSELECTIVE SYNTHESIS OF KETONES FROM CARBOXYLIC ACIDS AND GRIGNARD REAGENTS USING DICHLOROTRIPHENYLPHOSPHORANE
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Dichlorotriphenylphosphorane was found to be a good condensation reagent for synthesis of ketones from carboxylic acids and Grignard reagents under mild conditions.Synthetic utility of the present method is demonstrated by the chemoselective reaction of carboxylic acids possessing such a functional group as halogen, cyano, or carbonyl.
- Fujisawa, Tamotsu,Iida, Sachio,Uehara, Hiroshi,Sato, Toshio
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p. 1267 - 1270
(2007/10/02)
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- HIGHLY CHEMOSELECTIVE SYNTHESIS OF KETONES FROM CARBOXYLIC ACIDS AND GRIGNARD REAGENTS USING α-CHLOROENAMINES AS A CONDENSATION REAGENT
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α-Chloroenamines are found to be an effective condensation reagent of carboxylic acids and Grignard reagents under mild conditions to afford chemoselectively the corresponding ketones in high yields and in one-pot operation.
- Fujisawa, Tamotsu,Mori, Toshiki,Higuchi, Kazunobu,Sato, Toshio
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p. 1791 - 1794
(2007/10/02)
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- ONE-POT SYNTHESIS OF KETONES FROM CARBOXYLIC ACIDS AND GRIGNARD REAGENTS USING N,N-DIPHENYL-p-METHOXYPHENYLCHLOROMETHYLENIMINIUM CHLORIDE
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N,N-Diphenyl-p-methoxyphenylchloromethyleniminium chloride is found to be an effective condensation reagent of carboxylic acids and Grignard reagents under mild conditions to afford the corresponding ketones in high yields.
- Fujisawa, Tamotsu,Mori, Toshiki,Sato, Toshio
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p. 5059 - 5062
(2007/10/02)
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- A General Synthesis of Ketones from Alkenes via Stepwise Hydroboration with Thexylchloroborane
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Thexylalkylchloroboranes, reduced in the presence of a second alkene, produced mixed thexyldialkylboranes in high purity.These derivatives are readily transformed into the corresponding ketones by carbonylation or cyanidation, providing for the first time a general conversion of two different olefins into the corresponding ketone.
- Kulkarni, Surendra U.,Lee, Hsiupu D.,Brown, Herbert C.
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p. 4542 - 4543
(2007/10/02)
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