39248-99-2Relevant academic research and scientific papers
Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light
Zhang, Yueteng,Ji, Peng,Hu, Wenbo,Wei, Yongyi,Huang, He,Wang, Wei
supporting information, p. 8225 - 8228 (2019/07/16)
A metal- and oxidant-free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10-phenanthrenequinone-promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late-stage modification of complex structures, which are difficult to achieve with the existing protocols.
Synthesis of thiol esters using nano CuO/Ionic liquid as an eco-friendly reductive system under microwave irradiation
Azeredo, Juliano B.,Godoi, Marcelo,Schwab, Ricardo S.,Botteselle, Giancarlo V.,Braga, Antonio L.
supporting information, p. 5188 - 5194 (2013/11/06)
We report an efficient, fast, and environmentally friendly method for the synthesis of a wide range of thiol esters using stable diorganoyl disulfides and acyl chlorides, using CuO nanoparticles and [pmim]Br as the reductive system. This method gave good to excellent isolated yields of the desired products after only three minutes of microwave irradiation. Furthermore, by using the same green approach, we were also able to synthesize thiocarbonates bearing interesting functionalities. We report an efficient, fast, and environmentally friendly method for the synthesis of thiol esters starting from diorganoyl disulfides and acyl chlorides, and using CuO nanoparticles and [pmim]Br as the reductive system. This approach gave good to excellent isolated yields of the desired products in only three minutes under microwave irradiation. Copyright
Aminolysis of S-4-nitrophenyl X-substituted thiobenzoates: Effect of nonleaving-group substituents on reactivity and mechanism
Im, Li-Ra,Jeon, Sang-Eun,Um, Ik-Hwan
, p. 1153 - 1157 (2011/11/12)
A kinetic study is reported for aminolysis of S-4-nitrophenyl X-substituted thiobenzoates 3a-g in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. Thiol esters 3a-g are 7.8-47.6 fold more reactive than the corresponding oxygen esters (i.e., 4-nitrophenyl X-substituted benzoates 1a-g). Such reactivity order appears to be in accordance with the expectation that 4-nitrothiophenoxide in 3a-g is a better nucleofuge than 4-nitrophenoxide in 1a-g since the former is 2.64 pKa units less basic than the latter. Hammett plot for the reactions of 3a-g exhibit poor correlation coefficients (R2 = 0.977-0.986) with negative deviation by substrates possessing an electrondonating group (EDG), while the Yukawa-Tsuno plots result in excellent linear correlation (R2 = 0.995-0.997) with ? = 0.93-1.23 and r = 0.57-0.67, indicating that the negative deviation shown by substrates possessing an EDG is caused by ground-state stabilization through resonance interactions but not due to a change in ratedetermining step upon changing the nonleaving-group substituent X. The p value increases as the incoming amine becomes more basic and more reactive, indicating that the RSP is not operative in the current reactions.
Transition-metal-catalyzed regioselective aroyl- and trifluoro- acetylthiolation of alkynes using thioesters
Minami, Yasunori,Kuniyasu, Hitoshi,Miyafuji, Kiyoshi,Kambe, Nobuaki
experimental part, p. 3080 - 3082 (2009/12/01)
Intermolecular CO-retained carbothiolation of alkynes using thioesters took place to afford β-SR substituted enone derivatives; the choice of catalyst (Pd(dba)2-dppe) and the introduction of a CF3 group into the thioesters are the key to achieving the transformation. The Royal Society of Chemistry 2009.
