68634-32-2Relevant academic research and scientific papers
Thiophene synthesis via 1,1-carboboration
Eller, Christina,Kehr, Gerald,Daniliuc, Constantin G.,Stephan, Douglas W.,Erker, Gerhard
supporting information, p. 7226 - 7229 (2015/04/27)
Reaction of bis(tert-butylethynyl)sulfide with the boron Lewis acid reagents X-B(C6F5)2 (X = CH3, Cl, C6F5) in pentane at r.t. gave the respective borylated thiophenes in a sequence of 1,1-
Fast and highly chemoselective alkynylation of thiols with hypervalent iodine reagents enabled through a low energy barrier concerted mechanism
Frei, Reto,Wodrich, Matthew D.,Hari, Durga Prasad,Borin, Pierre-Antoine,Chauvier, Clment,Waser, Jrme
, p. 16563 - 16573 (2015/01/09)
Among all functional groups, alkynes occupy a privileged position in synthetic and medicinal chemistry, chemical biology, and materials science. Thioalkynes, in particular, are highly useful, as they combine the enhanced reactivity of the triple bond with a sulfur atom frequently encountered in bioactive compounds and materials. Nevertheless, general methods to access these compounds are lacking. In this article, we describe the mechanism and full scope of the alkynylation of thiols using ethynyl benziodoxolone (EBX) hypervalent iodine reagents. Computations led to the discovery of a new, three-atom concerted transition state with a very low energy barrier, which rationalizes the high reaction rate. On the basis of this result, the scope of the reaction was extended to the synthesis of aryl- and alkyl-substituted alkynes containing a broad range of functional groups. New sulfur nucleophiles such as thioglycosides, thioacids, and sodium hydrogen sulfide were also alkynylated successfully to lead to the most general and practical method yet reported for the synthesis of thioalkynes.
One-pot preparation of arylethynyl sulfides and bis(arylethynyl) sulfides
Su, Qiong,Zhao, Zi-Jian,Xu, Feng,Lou, Peng-Cai,Zhang, Kai,Xie, De-Xun,Shi, Lei,Cai, Qing-Yun,Peng, Zhi-Hong,An, De-Lie
, p. 1551 - 1557 (2013/04/23)
An efficient preparation for arylethynyl sulfides 1 and bis(arylethynyl) sulfides 2 has been accomplished through a one-pot, three-step strategy that starts from arylethanonyl sulfides and bis(arylethanonyl) sulfides, respectively, without the use of various terminal arylacetylenes as substrates. When lithium hexamethyldisilazane (LHMDS), ClP(O)(OEt)2, and LHMDS were sequentially added to a tetrahydrofuran solution of different substrates [arylethanonyl sulfides or bis(arylethanonyl) sulfides], 1 or 2 were obtained in moderate to good yields. The reaction procedure involves the formation of an enol phosphate and a subsequent base-induced elimination. An efficient preparation of arylethynyl sulfides 1 and bis(arylethynyl) sulfides 2 has been accomplished by a one-pot, three-step strategy that starts from arylethanonyl sulfides and bis(arylethanonyl) sulfides, respectively, to give 1 and 2 in moderate to good yields. The reaction mechanism involves the formation of an enol phosphate that undergoes a subsequent base-induced elimination. Copyright
Synthesis of alkynyl sulfides resulting from a novel ring cleavage of 5-chloro-1,2,3-thiadiazoles in the presence of organometallic reagents
Voets, Marieke,Smet, Mario,Dehaen, Wim
, p. 1473 - 1475 (2007/10/03)
5-Chloro-1,2,3-thiadiazoles 2a,b were treated with organolithium and Grignard reagents giving a novel ring cleavage with the loss of nitrogen and chloride anion, resulting in the formation of alkynyl sulfides 9-14. The results indicate that the mechanism of the reaction involves a concerted trans-elimination of the leaving group.
Synthese und Koordinationsverhalten von Di(1-phenyl-ethinyl)-Sulfan
Herres, Mathias,Walter, Olaf,Lang, Heinrich,Hosch, Ralf,Hahn, Josef
, p. 237 - 240 (2007/10/02)
The synthesis of S(CCPh)2 (III) is described.Compound III reacts with one equivalent octacarbonyldicobalt (IV) to yield (PhCC)S2-CCPh)Co2(CO)6> (V); with another equivalent of Co2(CO)8 (IV) the di-coordinated compound S2/su
