16616-39-0Relevant articles and documents
Organoborane-catalyzed selective 1,2-reduction of alkynones with hydride transfer: Synthesis of benzyl alkynes
Li, Huilin,Man, Qinghong,Ren, Yangqing,She, Xuegong,Wang, Lei,Yang, Mingyu,Yang, Zhigang,Zhai, Lele
supporting information, (2022/01/28)
Benzyl alkynes are important organic building blocks in organic synthesis. We report herein a B(C6F5)3-catalyzed site-selective 1,2-reduction of readily available alkynones to access benzyl alkyne derivatives. Under the de
Synthesis of (: Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid
Da Silva, Vitor A. F.,Da Silva, Gustavo P.,Matsuo, Bianca T.,Ali, Akbar,Davis, Rebecca L.,Zukerman-Schpector, Julio,Corrêa, Arlene G.,Paix?o, Márcio W.
supporting information, p. 519 - 526 (2019/01/24)
A convenient and broadly applicable method for the hydrohalogenation of ynones is described, by the combination of halotrimethylsilanes and tetrafluoroboric acid. Practically, one equivalent of HX (Br?nsted acid) and BF3 (Lewis acid) is smoothly generated, which activates the carbonyl compounds. Through this protocol, 42 examples of (Z)-β-halovinyl carbonyl compounds (Cl, Br and I) were obtained, in good yields and high stereoselectivity having 2-MeTHF as a solvent.
Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions
Meng, Mengting,Wang, Guofang,Yang, Liangfeng,Cheng, Kai,Qi, Chenze
, p. 1218 - 1231 (2018/02/16)
Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α-keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones bearing various substituents could be easily obtained. The introduction of hydroxyl substituent on ortho-site of α-keto acids make this strategy further applicable to the construction of flavone derivatives via heteroannulation in moderate to good yields with a similar silver-catalyzed system. The reactions proceed under relatively mild reaction conditions and tolerate a wide variety of functional groups. Control experiments indicated that both the reactions undergo radical processes. (Figure presented.).
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
Phosphane-ligated ionic palladium complexes: Synthesis, characterization and application as efficient and reusable precatalysts for the homogeneous carbonylative sonogashira reaction under CuI-free conditions
Zhang, Jing,Wang, Yongyong,Zhao, Xiaoli,Liu, Ye
, p. 975 - 985 (2015/04/27)
The stable ionic PdII complexes 1A-4A were synthesized through the complexation of PdCl2(MeCN)2 with the phosphane-functionalized ionic liquids (FILs) 1-4 with π-acceptor character. Single-crystal X-ray diffraction analyses showed that 1A-4A were all composed of PdII-centred square-planar cations and triflate (OTf-, CF3SO3-) counteranions. The complex cations in 1A-3A possessed structural similarity to trans-PdCl2(PPh3)2. The cation in 4A was a new PdII-centered planar complex ligated by the phosphane-carbon anion-carbene (PCC) pincer in a tripodal manner. The stabilities of 1A-4A were improved due to the intensive π-backbonding interaction between the Pd and P atoms. When complexes 1A-4A were used as precatalysts for homogeneous carbonylative Sonogashira coupling of PhI with phenylacetylene free of CuI, 1A-3A exhibited excellent catalytic behaviour with a TON of up to 1700 at a CO pressure of 0.5 MPa and moderate temperature of 100 °C, whereas 4A exhibited poor activity towards the transformation of PhI due to the high stability of 4A. The recycling experiments of 3A in [Bpy]BF4 (as a solvent) indicated that 3A could be recycled for 5 runs with neither activity loss nor metal leaching into the organic phase. Complex 3A also proved to be a general precatalyst for the carbonylative Sonogashira couplings of a wide range of aryl iodides with phenylacetylene. The selectivity of the desired carbonylation product depended more on electronic effects than the steric effects of the substituents of the aryl iodides.
Phosphane-ligated ionic palladium complexes: Synthesis, characterization and application as efficient and reusable precatalysts for the homogeneous carbonylative sonogashira reaction under CuI-free conditions
Zhang, Jing,Wang, Yongyong,Zhao, Xiaoli,Liu, Ye
, p. 975 - 985 (2014/03/21)
The stable ionic PdII complexes 1A-4A were synthesized through the complexation of PdCl2(MeCN)2 with the phosphane-functionalized ionic liquids (FILs) 1-4 with π-acceptor character. Single-crystal X-ray diffraction analyses showed that 1A-4A were all composed of PdII-centred square-planar cations and triflate (OTf-, CF3SO3-) counteranions. The complex cations in 1A-3A possessed structural similarity to trans-PdCl2(PPh 3)2. The cation in 4A was a new PdII-centered planar complex ligated by the phosphane-carbon anion-carbene (PCC) pincer in a tripodal manner. The stabilities of 1A-4A were improved due to the intensive π-backbonding interaction between the Pd and P atoms. When complexes 1A-4A were used as precatalysts for homogeneous carbonylative Sonogashira coupling of PhI with phenylacetylene free of CuI, 1A-3A exhibited excellent catalytic behaviour with a TON of up to 1700 at a CO pressure of 0.5 MPa and moderate temperature of 100 °C, whereas 4A exhibited poor activity towards the transformation of PhI due to the high stability of 4A. The recycling experiments of 3A in [Bpy]BF4 (as a solvent) indicated that 3A could be recycled for 5 runs with neither activity loss nor metal leaching into the organic phase. Complex 3A also proved to be a general precatalyst for the carbonylative Sonogashira couplings of a wide range of aryl iodides with phenylacetylene. The selectivity of the desired carbonylation product depended more on electronic effects than the steric effects of the substituents of the aryl iodides. The ionic palladium complexes 1A-4A ligated by imidazolium-based-phosphanes were prepared and shown, by single-crystal X-ray diffraction analyses, to be composed of PdII-centered square-planar cations and OTf- counteranions. The complexes were tested as precatalysts for the homogeneous carbonylative Sonogashira coupling of aryl iodides with phenylacetylene. Copyright
A Highly Active CuI/TMEDA Catalytic System for the Coupling Reaction of Acid Chlorides with Terminal Alkynes under Solvent-Free Conditions
Yin, Weiyan,He, Haifeng,Zhang, Yani,Luo, Di,He, Hongwu
, p. 2617 - 2621 (2015/12/26)
A highly efficient copper(I) iodide/N,N,N′,N′-tetramethylethylenediamine (CuI/TMEDA) catalytic system for the synthesis of ynones has been developed. A variety of terminal alkynes, including 4-iodophenylacetylene, were smoothly coupled with acid chlorides
Synthesis of phosphonylated and thiolated indenones by manganese(III)- mediated addition of phosphorus- and sulfur-centered radicals to 1,3-diarylpropynones
Zhou, Jun,Zhang, Guang-Liang,Zou, Jian-Ping,Zhang, Wei
supporting information; experimental part, p. 3412 - 3415 (2011/09/12)
Phosphorus- or sulfur-centered radicals generated from the reaction of manganese(III) acetate with dialkyl phosphonates or arylthiols undergo selective additions to conjugated alkynes followed by cyclization and rearomatization to afford 2-phosphonyl- or
Silica-supported zinc bromide (ZnBr2/SiO2): A highly efficient heterogeneous catalyst for coupling acid chlorides with terminal alkynes
Keivanloo, Ali,Bakherad, Mohammad,Bahramian, Bahram,Baratnia, Samaneh
experimental part, p. 1498 - 1502 (2011/05/16)
Silica-supported zinc bromide (ZnBr2/SiO2) is an efficient heterogeneous catalyst for the rapid synthesis of ynones by cross-coupling of acid chlorides with terminal alkynes in good to excellent yields under solvent-free conditions a
