245322-93-4Relevant academic research and scientific papers
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.
Combining Electronic and Steric Effects to Generate Hindered Propargylic Alcohols in High Enantiomeric Excess
Vyas, Vijyesh K.,Knighton, Richard C.,Bhanage, Bhalchandra M.,Wills, Martin
supporting information, p. 975 - 978 (2018/02/23)
Tethered ruthenium-TsDPEN complexes have been applied to the catalysis of the asymmetric transfer hydrogenation of a range of aryl/acetylenic ketones. The introduction of an ortho- substituent to the aryl ring of the substrate results in a reversal of the
Divergence in Ynone Reactivity: Atypical Cyclization by 3,4-Difunctionalization versus Rare Bis(cyclization)
Alcaide, Benito,Almendros, Pedro,Lázaro-Milla, Carlos,Delgado-Martínez, Patricia
supporting information, p. 8186 - 8194 (2018/06/15)
Functionalized ynones can be activated by Tf2C=CH2, which was generated in situ, to form zwitterionic species. These species were trapped in an intramolecular fashion by several nucleophiles to generate two major types of triflones in a divergent manner. Through fine-tuning of the reaction temperature, bis(triflyl)-6-membered- or (triflyl)-5-membered-fused-heterocycles were achieved in reasonable yields in a totally selective manner. In this way, bis(triflyl)flavones, bis(triflyl)thioflavones, bis(triflyl)selenoflavones, (triflyl)benzothienopyrans, (triflyl)benzoselenophenopyrans, (triflyl)vinyl aurones, and (triflyl)pyranoindoles were constructed. Conceivable mechanistic pathways were suggested on the basis of the isolation of several intermediates and the results from control experiments.
Regioselective Synthesis of Heteroatom-Functionalized Cyclobutene-triflones and Cyclobutenones
Alcaide, Benito,Almendros, Pedro,Lázaro-Milla, Carlos
supporting information, p. 2630 - 2639 (2017/08/16)
The controlled metal-free synthesis of a vast variety of heteroatom-containing cyclobutene-triflones [bis(trifluoromethylsulfonyl)cyclobutenes] and cyclobutenones has been developed starting from heteroatom-substituted alkynes and a pyridinium salt (a latent Tf2C=CH2 source). This powerful methodology, involving cyclization reactions, allows for the selective preparation of oxygen-, nitrogen-, bromine-, chlorine-, iodine-, sulfur-, selenium-, tellurium-, phosphorus-, and silicon-functionalized cyclobutene derivatives. (Figure presented.).
Highly Efficient Synthesis of Multi-Substituted Allenes from Propargyl Acetates and Organoaluminum Reagents Mediated by Palladium
Zhang, Zhen,Shao, Xuebei,Zhang, Gang,Li, Qinghan,Li, Xinying
, p. 3643 - 3653 (2017/08/16)
A simple and mild catalytic S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents is reported. The S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents mediated by Pd(PhP 3) 2 Cl 2 (1 mol%)/PPh 3 (2 mol%)/K 2 CO 3 in tetrahydrofuran at 60 °C for 3-4 hours afforded the corresponding multi-substituted allenes in good yields (up to 94%) with high selectivities (up to 99%). The process was simple and easily performed, which offers an efficient method to synthesize the multi-substituted allene derivatives.
Addition of terminal alkynes to α-ketone esters to synthesize α-tertiary-hydroxy esters promoted by zinc and an alkyl halide
Zhang, Wen,Cao, Yuan,Chen, Wei,Zhao, Gang,Pu, Lin
supporting information, p. 6430 - 6432 (2015/11/16)
A convenient method to synthesize various α-tertiary-hydroxy esters at room temperature has been developed. This method uses the readily available and inexpensive Zn powder in combination with an alkyl halide to promote the addition of alkynes to α-ketone
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
Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes
Karakaya, Idris,Karabuga, Semistan,Altundas, Ramazan,Ulukanli, Sabri
supporting information, p. 8385 - 8388 (2015/03/05)
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
Synthesis of 1,3-thioxoketones from salicylaldehyde
Semenova,Yarovenko,Levchenko,Krayushkin
, p. 1022 - 1025 (2014/03/21)
A method for the synthesis of monothiodibenzoylmethanes was developed. The method involves a reaction of potassium thioacetate with 1-(2-hydroxyphenyl)-3- phenylpropynone prepared from salicylaldehyde.
Tetrabutylammonium fluoride (TBAF)-catalyzed addition of substituted trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones
Chintareddy, Venkat Reddy,Wadhwa, Kuldeep,Verkade, John G.
supporting information; experimental part, p. 4482 - 4488 (2011/07/30)
Herein we report that tetrabutylammonium fluoride (TBAF) is a very efficient catalyst for the addition of trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones in THF solvent at room temperature. The reaction conditions are mild and oper
