479213-87-1Relevant academic research and scientific papers
Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes
Karakaya, Idris,Karabuga, Semistan,Altundas, Ramazan,Ulukanli, Sabri
, p. 8385 - 8388 (2014)
Five novel 4-phenylquinazolinols were synthesised in three steps. Their application as ligands in the titanium tetraisopropoxide promoted catalytic enantioselective addition of phenylacetylene to a variety of aldehydes gave propargylic alcohols. Under the
DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives
De, Rimpa,Savarimuthu, Antony,Ballav, Tamal,Singh, Pijush,Nanda, Jayanta,Hasija, Avantika,Chopra, Deepak,Bera, Mrinal K.
supporting information, p. 1587 - 1592 (2020/08/28)
A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer-Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated and found to be of interest.
Catalytic claisen rearrangement by intercepting ketenimines with propargylic alcohols: A strategy to generate and transform ketenimines from radicals
Yan, Xuyang,Liu, Hongchi,Wei, Shenquan,Huang, Hanmin
supporting information, p. 6794 - 6798 (2020/09/15)
An efficient strategy for facilitating the cross-coupling of two radicals has been established via the coordination of a radical with a metal catalyst. This strategy provides a remarkable ability to harness the reactivity of nitrile-containing azoalkanes and enables a novel cascade reaction with nitrile-containing azoalkanes and propargylic alcohols to be established. By using this reaction, a range of acetylenic and allenic amides were obtained that provides a versatile platform for further derivatizations.
Highly regioselective gold-catalyzed formal hydration of propargylic: Gem -difluorides
Hamel, Jean-Denys,Hayashi, Tatsuru,Cloutier, Mélissa,Savoie, Paul R.,Thibeault, Olivier,Beaudoin, Meggan,Paquin, Jean-Fran?ois
supporting information, p. 9830 - 9836 (2017/12/08)
Herein, we report a highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides. Not only does this transformation provide access to versatile fluorinated building blocks that were difficult or hardly possible to access beforehand, but it also represents a rare case of a highly regioselective gold-catalyzed hydroalkoxylation of internal alkynes and puts forward the utility of the difluoromethylene unit as a directing group in catalysis.
Palladium-catalyzed nucleophilic substitution of propargylic carbonates and meldrum's acid derivatives
Ambrogio, Ilaria,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Iazzetti, Antonia
, p. 3147 - 3151 (2015/05/13)
The palladium-catalyzed reaction of propargylic carbonates with Meldrum's acid derivatives proceeds smoothly in the presence of Pd(OAc)2 and P(2-furyl)3 in THF at 80 °C to give substitution products. The substitution products can be
Direct synthesis of 4-fluoroisoxazoles through gold-catalyzed cascade cyclization-fluorination of 2-alkynone O-methyl oximes
Jeong, Yunkyung,Kim, Bom-I,Lee, Jae Kyun,Ryu, Jae-Sang
, p. 6444 - 6455 (2014/08/05)
A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl oximes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol
A convenient approach to β-heteroarylated (C-N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles
Bhanuchandra,Kuram, Malleswara Rao,Sahoo, Akhila K.
experimental part, p. 3538 - 3555 (2012/05/20)
An efficient and direct approach to β-heteroarylated (C-N bond) ketones is demonstrated. Base promoted redox isomerization of propargyl alcohol to α,β-unsaturated ketone followed by conjugate addition to NH-heteroarenes affords a wide range of β-heteroarylated ketones in good to excellent yields. Aryl, heteroaryl, alkyl C(sp), and terminal alkynes containing unactivated propargyl alcohols effectively undergo redox-isomerization conjugate addition (RICA) with NH-heteroarenes. Reaction of 3-substituted pyrazoles or indazole with propargyl alcohols enables highly regioselective products. A diverse range of NH-bearing nucleophiles such as: pyrazoles, imidazole, triazoles, pyrrole, indoles and aniline participate in this reaction and deliver the corresponding β-heteroarylated ketones.
P(PhCH2NCH2CH2)3N: An efficient Lewis base catalyst for the synthesis of propargylic alcohols and Morita-Baylis-Hillman adducts via aldehyde alkynylation
Wadhwa, Kuldeep,Chintareddy, Venkat Reddy,Verkade, John G.
supporting information; experimental part, p. 6681 - 6690 (2009/12/30)
(Chemical Equation Presented) Proazaphosphatrane P(PhCH2NCH 2CH2)3N (1a) is an efficient catalyst for the addition of aryl trimethylsilyl alkynes to a variety of aromatic, aliphatic, and heterocyclic aldehydes i
Au(PPh3)Cl-AgSbF6-catalyzed rearrangement of propargylic 1,3-dithianes: Formation of 8-membered 1,3-bisthio-substituted cyclic allenes
Zhao, Xia,Zhong, Zhenzhen,Peng, Lingling,Zhang, Wenxiong,Wang, Jianb
supporting information; experimental part, p. 2535 - 2537 (2009/09/30)
Au(PPh3)Cl-AgSbF6-catalyzed rearrangement of propargylic 1,3-dithiane leads to the formation of 8-membered dithio-substituted cyclic allenes, which are remarkably stable. The Royal Society of Chemistry 2009.
Catalytic enantioselective addition of terminal alkynes to aromatic aldehydes using zinc-hydroxyamide complexes
Blay, Gonzalo,Cardona, Luz,Fernandez, Isabel,Marco-Aleixandre, Alicia,Munoz, M. Carmen,Pedro, Jose R.
scheme or table, p. 4301 - 4308 (2009/12/05)
A mandelamide ligand, derived from (S)-mandelic acid and (S)-phenylethanamine, catalyzes the addition of aryl-, alkyl- and silyl-alkynylzinc reagents to aromatic and heteroaromatic aldehydes with good yields and good to high enantioselectivities.
