1255152-53-4Relevant academic research and scientific papers
Transition-Metal-Free Synthesis of Ynones via Decarboxylative Alkynylation of α-Keto Acids under Mild Conditions
Wang, Peng-Fei,Feng, Yi-Si,Cheng, Zhi-Fei,Wu, Qiu-Min,Wang, Guang-Yu,Liu, Liang-Liang,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian
, p. 9314 - 9320 (2015)
A transition-metal-free synthetic method of various ynones via decarboxylative alkynylation of α-keto acids is described. The reaction is carried out under mild conditions and exhibits remarkable tolerance of functional groups. The mechanism of a radical
Selective Carbonyl?C(sp3) Bond Cleavage To Construct Ynamides, Ynoates, and Ynones by Photoredox Catalysis
Jia, Kunfang,Pan, Yue,Chen, Yiyun
supporting information, p. 2478 - 2481 (2017/02/23)
Carbon–carbon bond cleavage/functionalization is synthetically valuable, and selective carbonyl?C(sp3) bond cleavage/alkynylation presents a new perspective in constructing ynamides, ynoates, and ynones. Reported here is the first alkoxyl-radical-enabled carbonyl?C(sp3) bond cleavage/alkynylation reaction by photoredox catalysis. The use of novel cyclic iodine(III) reagents are essential for β-carbonyl alkoxyl radical generation from β-carbonyl alcohols, including alcohols with high redox potential (EoxP>2.2 V vs. SCE in MeCN). β-Amide, β-ester, and β-ketone alcohols yield ynamides, ynoates, and ynones, respectively, for the first time, with excellent regio- and chemoselectivity under mild reaction conditions.
Metal-free synthesis of ynones via direct C-H alkynylation of aldehydes with ethynylbenziodoxolones
Zhang, Ruo-Yi,Xi, Long-Yi,Zhang, Lei,Chen, Shan-Yong,Yu, Xiao-Qi
, p. 6176 - 6182 (2015/08/03)
Abstract A metal-free synthesis of ynones via direct alkynlyation of C-H bonds in aldehydes with ethynylbenziodoxolones is described. A variety of unactivated aldehydes undergo this transformation, affording ynones in good yields. These ynones could be fu
Decarboxylative Alkynylation of α-Keto Acids and Oxamic Acids in Aqueous Media
Wang, Hua,Guo, Li-Na,Wang, Shun,Duan, Xin-Hua
supporting information, p. 3054 - 3057 (2015/06/30)
A mild K2S2O8 promoted decarboxylative alkynylation of α-keto acids and oxamic acids has been developed. This process features mild reaction conditions, a broad substrate scope, and good functional-group tolerance, therefo
Cinchona alkaloid-catalyzed asymmetric trifluoromethylation of alkynyl ketones with trimethylsilyl trifluoromethane
Kawai, Hiroyuki,Tachi, Kentaro,Tokunaga, Etsuko,Shiro, Motoo,Shibata, Norio
supporting information; experimental part, p. 5104 - 5107 (2010/12/29)
The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me4NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.
