144486-12-4Relevant academic research and scientific papers
Investigation into the Allylation Reactions of Aldehydes Promoted by the CeCl3·7H2O-NaI System As A Lewis Acid
Bartoli, Giuseppe,Bosco, Marcella,Giuliani, Arianna,Marcantoni, Enrico,Palmieri, Alessandro,Petrini, Marino,Sambri, Letizia
, p. 1290 - 1297 (2004)
The Lewis acid promoted allylation of aldehydes has become an important carbon-carbon bond forming reaction in organic chemistry. In this context, we have developed an alternative over existing catalytic processes, wherein aldehydes are subject in acetoni
Organometallic reactions in aqueous media. Antimony-mediated allylation of carbonyl compounds with fluoride salts
Li, Lian-Hai,Chan, Tak Hang
, p. 5009 - 5012 (2000)
Commercial antimony can be used directly for the allylation of carbonyl compounds in aqueous media in the presence of fluoride salts. (C) 2000 Elsevier Science Ltd.
Waste management in zinc promoted allylation of aldehyde
Pratihar, Sanjay,Kakoty, Anindita,Sarmah, Kasturi
, p. 5347 - 5356 (2016)
By using an efficient, sustainable and green procedure, the waste zinc material in Zn(0) promoted Grignard-Barbier type allylation of aldehydes has been successfully utilized as a reusable material for the adsorption of various dyes and also converted int
Do more electrophilic aldehydes/ketones exhibit higher reactivity toward nucleophiles in the presence of Lewis acids?
Asao, Naoki,Asano, Toru,Yamamoto, Yoshinori
, p. 3206 - 3208 (2001)
A crucial role in the chemoselective synthesis of primary, secondary, and homoallylic alcohols and of Diels-Alder adducts is played by Lewis acids (LA) in the addition of nucleophiles (Nu) to carbonyl compounds (see scheme; EWG = electron-withdrawing group, EDG = electron-donating group).
Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes
Fu, Xiao-Yang,Si, Ya-Feng,Qiao, Li-Peng,Zhao, Yu-Fen,Chen, Xiao-Lan,Yu, Bing
supporting information, p. 574 - 580 (2021/11/13)
A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.
Gold(I)-Catalyzed Intramolecular Dehydrative Amination of Sulfamate Esters Tethered to Allylic Alcohols: A Strategy for the Synthesis of Cyclic Sulfamidates
Park, Yunjeong,Lee, Ji Sun,Ryu, Jae-Sang
supporting information, p. 2183 - 2188 (2021/03/15)
An efficient synthesis protocol for cyclic sulfamidates has been developed via catalytic intramolecular cyclizations of sulfamate esters tethered to allylic alcohols. The reactions proceed smoothly at room temperature in the presence of (IPr)AuCl (5 mol%) and AgBF4 (5 mol%). This protocol features good to excellent yields, high selectivity, broad substrate scope, and mild reaction conditions. This method is also applicable to the synthesis of a seven-membered sulfamidate. (Figure presented.).
Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions
Potenti, Simone,Gualandi, Andrea,Puggioli, Alessio,Fermi, Andrea,Bergamini, Giacomo,Cozzi, Pier Giorgio
supporting information, p. 1624 - 1627 (2021/02/05)
Organometallic allylic reagents are widely used in the construction of C?C bonds by Barbier-type reactions. In this communication, we have described a photoredox Barbier allylation of aldehydes mediated by bismuth, in absence of other metals as co-reductants. Mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.
Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines
He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng
supporting information, (2021/05/31)
A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.
Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems
Apolinar, Omar,Derosa, Joseph,Engle, Keary M.,Karunananda, Malkanthi K.,Kleinmans, Roman,Li, Zi-Qi,Tran, Van T.,Wisniewski, Steven R.
supporting information, p. 5311 - 5316 (2021/07/26)
A nickel-catalyzed 1,2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis reveals the effect of electronic factors on initial rates.
Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex
Gualandi, Andrea,Rodeghiero, Giacomo,Perciaccante, Rossana,Jansen, Thomas Paul,Moreno-Cabrerizo, Cristina,Foucher, Charles,Marchini, Marianna,Ceroni, Paola,Cozzi, Pier Giorgio
supporting information, p. 1105 - 1111 (2021/01/04)
The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr2 (10 mol %), 4,4′-di-tert-butyl-2,2′-dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy)2]PF6 (ppy=2-phenylpyridine, 2 mol %), and N,N-diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported. (Figure presented.).
