58686-72-9Relevant academic research and scientific papers
Rhodium-catalyzed enantioselective decarboxylative alkynylation of allenes with arylpropiolic acids
Grugel, Christian P.,Breit, Bernhard
supporting information, p. 1066 - 1069 (2018/02/23)
A rhodium-catalyzed chemo-, regio-, and enantioselective intermolecular decarboxylative alkynylation of terminal allenes with arylpropiolic acids is reported. Employing a Rh(I)/(R)-Tol-BINAP catalytic system, branched allylic 1,4-enynes were obtained under mild conditions. The overall utility of this protocol is exemplified by a broad functional group compatibility.
Rh-Catalyzed Asymmetric Hydrogenation of β-Substituted-β-thio-α,β-unsaturated Esters: Expeditious Access to Chiral Organic Sulfides
Liu, Gang,Han, Zhengyu,Dong, Xiu-Qin,Zhang, Xumu
supporting information, p. 5636 - 5639 (2018/09/12)
Rh/bifunctional bisphosphine-thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydorgenation of both (Z)- and (E)-isomers of β-substituted-β-thio-α,β-unsaturated esters was successfully developed. This new asymmetric catalytic methodology provided highly efficient access to two enantiomers of chiral organic sulfides ethyl β-substituted-β-thio-propanoates with excellent results (up to 99% yield and >99% ee for (Z)-substrates, up to 99% yield and 98% ee for (E)-substrates, TON up to 5000), which are important intermediates in organic synthesis.
Gold(I)/Chiral N,N′-Dioxide–Nickel(II) Relay Catalysis for Asymmetric Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement
Li, Jun,Lin, Lili,Hu, Bowen,Zhou, Pengfei,Huang, Tianyu,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 885 - 888 (2017/01/13)
A highly efficient asymmetric cascade reaction between alkynyl esters and allylic alcohols has been realized. Key to success was the combination of a hydroalkoxylation reaction catalyzed by a π-acidic gold(I) complex with a Claisen rearrangement catalyzed by a chiral Lewis acidic N,N′-dioxide–nickel(II) complex. A range of acyclic α-allyl β-keto esters were synthesized in high yields (up to 99 %) with good diastereoselectivities (up to 97:3) and excellent enantioselectivities (up to 99 % ee) under mild reaction conditions. These products can be easily transformed into optically active β-hydroxy esters, β-hydroxy acids, or 1,3-diols.
Enantioselective synthesis of β-fluoro-β-aryl-α-aminopentenamides by organocatalytic [2,3]-sigmatropic rearrangement
Kasten, Kevin,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information, p. 5182 - 5185 (2017/11/06)
The tetramisole-promoted catalytic enantioselective [2,3]-sigmatropic rearrangement of quaternary ammonium salts bearing a (Z)-3-fluoro-3-arylprop-2-ene group generates, after addition of benzylamine, a range of β-fluoro-β-aryl-α-aminopentenamides containing a stereogenic tertiary fluorine substituent. Cyclic and acyclic nitrogen substituents as well as various aromatic substituents are tolerated, giving the β-fluoro-β-aryl-α-aminopentenamide products in up to 76% yield, 96:4 dr, and 98:2 er.
Visible-Light-Promoted Vinylation of Tetrahydrofuran with Alkynes through Direct C-H Bond Functionalization
Li, Jing,Zhang, Jing,Tan, Haibo,Wang, David Zhigang
supporting information, p. 2522 - 2525 (2015/05/27)
(Chemical Equation Presented) Mild and direct C-H bond functionalizations and vinylations of tetrahydrofuran with alkynes have been accomplished through visible light photocatalysis, yielding a range of vinyl tetrahydrofurans under the synergistic actions of organic dye-type photocatalyst eosin Y, tert-butyl hydroperoxide (t-BuOOH), and a 45 W household lightbulb. A significant kinetic isotope effect (KIE) was recorded, which helps shed light on the mechanistic course.
Gold catalysis coupled with visible light stimulation: Syntheses of functionalized indoles
Cai, Shunyou,Yang, Kai,Wang, David Zhigang
supporting information, p. 2606 - 2609 (2014/06/09)
A judicious combination of Au-catalysis and synergistic visible-light stimulation formulates an exceptionally simple and mild reaction system capable of directly coupling anilines and alkynes to form multifunctionalized indoles.
Synthesis of ethyl arylpropiolates through palladium-catalyzed cross-coupling reactions of aryl iodides with in situ generated lithium tetrakis(ethoxycarbonylethynyl)indates
Park, Youngchul,Kang, Dongjin,Jeon, Woo Hyung,Ryu, Taekyu,Lee, Phil Ho
, p. 2305 - 2311 (2014/11/08)
An efficient synthetic method to access ethyl arylpropiolates has been developed; it involves a palladium-catalyzed cross-coupling reaction between a wide range of aryl iodides and lithium tetrakis(ethoxycarbonylethynyl)indates (0.35 equiv) generated in situ from indium trichloride and alkynides obtained from ethyl propiolate and n-butyllithium. Georg Thieme Verlag Stuttgart. New York.
Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3- azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes
Durham, Robin,Mandel, Jeremie,Blanchard, Nicolas,Tam, William
scheme or table, p. 1494 - 1505 (2012/01/12)
Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3- azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes were investigated. Yields of up to 90% were obtained though regioselectivity was modest. Select cycloadducts could be separated and used to access a highly functionalized [3.2.0] bicyclic structure through reductive cleavage of the N-O bond. These ring-opened products displayed a chemical exchange phenomenon in 1D carbon NMR and required characterization by 2D NMR techniques.
Facile synthesis of substituted alkynes by nano-palladium catalyzed oxidative cross-coupling reaction of arylboronic acids with terminal alkynes
Nie, Xiaopeng,Liu, Suli,Zong, Yan,Sun, Peipei,Bao, Jianchun
experimental part, p. 1570 - 1573 (2011/06/17)
The oxidative cross-coupling of terminal alkynes with arylboronic acids catalyzed by the porous palladium nanospheres was developed. In the presence of silver oxide, triphenylphosphine and cesium carbonate, the reaction provided the corresponding arylalkynes with good to excellent yields. There were also other obvious advantages such as broad applicability, high selectivity, simple experimental operation as well as the convenient preparation, high efficiency and reusability of catalyst. The possible mechanism of this transition-metal nanoparticles catalyzed oxidative cross-coupling reaction of two nucleophiles was proposed.
Copper-catalyzed alkyne-aryne coupling reaction under microwave conditions: preparation of unsymmetric and symmetric di-substituted alkynes
Akubathini, Shashidhar Kumar,Biehl, Ed
scheme or table, p. 1809 - 1811 (2009/07/05)
Several unsymmetric and symmetric alkynes were prepared excellent to modest yields by generating benzyne from the reaction of 2-(trimethylsilyl)phenyl triflate with CsF in the presence of CuI and terminal alkyne under microwave heating for 30 min at 150 °
