116249-87-7Relevant academic research and scientific papers
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.
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.).
Photostimulated Reactions of Alkanethiolate Ions with Haloarenes. Electron Transfer vs. Fragmentation of the Radical Anion Intermediate
Rossi, Roberto A.,Palacios, Sara M.
, p. 5300 - 5304 (2007/10/02)
The photostimulated reactions of RS(1-) ions (R = methyl, n-butyl, tert-butyl, and benzyl) with haloarenes in liquid ammonia were studied.Two main products were formed: alkyl aryl sulfide and arenethiolate ions.The formation of these compounds is explained by the SRN1 mechanism of aromatic nucleophilic substitution.The radical anion intermediate formed in the coupling of an aryl radical with an alkanethiolate ion undergoes two competing reactions: transfer of the odd electron to the substrate leading to the substitution product or bond fragmentation leading to arenethiolate ion and an alkyl radical.It is concluded that the ratio of these products depends mainly on changes in the rate of fragmentation and not on changes in the electron-transfer reaction.
