58086-68-3Relevant academic research and scientific papers
Synthesis method of heteroaryl thioether
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Paragraph 0059-0062, (2020/08/30)
The invention discloses a synthesis method of heteroaryl thioether. Under the conditions of no catalyst, no solvent, no additive and the like, aryl halide/2-bromopyridine, thiourea and substituted benzyl bromide which are directly taken as raw materials to selectively synthesize asymmetric heteroaryl thioether in one step without using conventional organic sulfides such as mercaptan or thiophenol.The use of organic sulfides with high toxicity and heavy odor, such as mercaptan or thiophenol, is avoided, and the synthesis steps are shortened, so that the synthesis efficiency is improved, the reaction has good selectivity, and the asymmetric thioether can be preferentially obtained.
Promoting Effect of Crystal Water Leading to Catalyst-Free Synthesis of Heteroaryl Thioether from Heteroaryl Chloride, Sodium Thiosulfate Pentahydrate, and Alcohol
Ma, Xiantao,Yu, Jing,Yan, Ran,Yan, Mengli,Xu, Qing
, p. 11294 - 11300 (2019/09/12)
It is observed the crystal water in sodium thiosulfate pentahydrate (Na2S2O3·5H2O) can promote its multicomponent reaction with heteroaryl chlorides and alcohols, providing a facile, green, and specific synthesis of unsymmetrical heteroaryl thioethers via one-step formation of two C-S bonds under catalyst-, additive-, and solvent-free conditions. Mechanistic studies suggest that the crystal water in Na2S2O3·5H2O is crucial in generating the key thiol intermediates and byproduct NaHSO4, which then catalyzes the dehydrative substitution of alcohols with thiols to afford thioethers.
Utilizing 2-phenylpropanal as coupling partner for C-S bond formation via sequential thioarylation and decarbonylation process: A novel strategy for the synthesis of aryl alkyl sulfides
Shaikhi Shahidzadeh, Elham,Nowrouzi, Najmeh,Abbasi, Mohammad
, (2019/09/12)
In this study, first direct access to aryl alkyl sulfides employing 2-phenylpropanal as coupling partner is reported. Diaryl disulfides react with this aldehyde in the presence of morpholine and produce the corresponding sulfide products in high yields. In another part, disulfides are in situ generated in the reaction mixture from aryl halides/CuI/Cyanodithioformate and coupled with 2-phenylpropanal to access aryl alkyl sulfides.
Efficient Generation of C–S Bonds via a By-Product-Promoted Selective Coupling of Alcohols, Organic Halides, and Thiourea
Ma, Xiantao,Yu, Lei,Su, Chenliang,Yang, Yaqi,Li, Huan,Xu, Qing
supporting information, p. 1649 - 1655 (2017/05/29)
A metal- and base-free three-component coupling of alcohols, heteroaryl halides, and thiourea has been developed for direct and selective synthesis of heteroaryl thioethers. This method can be easily scaled up to the gram scale and extended to dialkyl thioethers, heteroaryl selenides, benzothiazoles, and some antimycobacterially-active thioethers. Mechanistic studies revealed that a by-product-promoted in situ C–O activation of alcohols to more reactive alkyl halides and slow release of the thiol and alkyl halide intermediates are the key to the high selectivity and success of the reaction. (Figure presented.).
Palladium and copper co-catalyzed Markovnikov hydrothiolation of terminal olefins and alkynes
Ma, Haojie,Ren, Xiaoyu,Zhou, Xiaoqiang,Ma, Chaowei,He, Yongqin,Huang, Guosheng
, p. 6022 - 6029 (2015/10/28)
A simple and efficient method for palladium and copper co-catalyzed Markovnikov hydrothiolation of thiols to olefins or alkynes has been developed. The reaction allows olefins or alkynes bearing various functional groups to react with different thiols, pr
CATALYTIC C-H BOND ACTIVATION FOR THE SYNTHESIS OF ETHERS AND THIOETHERS
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Page/Page column 49-50, (2014/01/08)
Disclosed is a method for the transition metal-mediated oxidation of C-H bonds to form C-0 or C-S bonds. The methods are useful for the formation of ethers (R-OR') from alcohols, R'OH, and sp3 -hybridized C-H bonds in substrates, R-H. Aryl or heteroaryl acetates may also be used for C-H to C-OAr bond formation. The methods are also useful in the preparation of C-S bonds from acetyl-protected thiols, MeC(0)SR, and disulfides, RSSR. Advantageously, the methods minimize reaction steps, the handling of oxidized intermediates, and environmental impact.
Conversion of Hydroxyl Groups in Alcohols to Other Functional Groups with N-Hydroxy-2-thiopyridone, and Its Application to Dialkylamines and Thiols
Togo, Hideo,Fujii, Misa,Yokoyama, Masataka
, p. 57 - 67 (2007/10/02)
The radical decarboxylation reaction of N-alkoxyoxalyloxy-2-thiopyridone which was prepared by the reaction of alcohol, oxalyl chloride, and N-hydroxy-2-thiopyridone was studied both in the absence and presence of olefinic compounds.The same reactions with olefinic and acetylenic alcohols gave the corresponding lactone derivatives.On the other hand the unsymmetrical alkyl 2-pyridyl disulfides were obtained by the same reaction with aliphatic thiols.
Some Studies on syn-Elimination Reactions
Crich, David,Lin, Linda B. L.
, p. 2928 - 2941 (2007/10/02)
On heating to 220 deg C the 2-alkylthiopyridine N-oxide (6) was found to undergo syn-elimination giving ethyl acrylate.Sulphoxide (15) was more prone to syn-elimination than sulphoxide (16) demonstrating the importance of β-hydrogen acidity in the rate of sulphoxide syn-eliminations.
