13333-97-6Relevant academic research and scientific papers
SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF
-
Paragraph 0032; 0033; 0063; 0067; 0069; 0070; 0074, (2017/09/02)
The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017
Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
Liu, Yajun,Kim, Jihye,Seo, Heesun,Park, Sunghyouk,Chae, Junghyun
supporting information, p. 2205 - 2212 (2015/07/27)
A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.
Metallation reactions XXII. Regioselective metallation of (trifluoromethyl) (alkylthio) benzenes
Cabiddu,Cabiddu,Cadoni,Corrias,Fattuoni,Floris,Melis
, p. 125 - 140 (2007/10/03)
The metallation reactions of (trifluoromethyl)(alkylthio)benzenes with organolithium reagents and with the butyllithium/potassium tert-butoxide superbasic mixture are here described. The results, according to the theoretical calculations of energy minima, show the monometallation regiochemistry is directed by the sulphur atom. On the other side, the bimetallation, that can be performed only on methylthio derivatives, depends on the organometallic reagent employed. Using butyllithium the stronger coordinative power of sulphur prevails and products metallated in ortho and alpha positions to this atom are mainly formed. With the more basic sec-butyllithium and with the Superbase, because of mutual competition between the thioalkyl and trifluoromethyl groups, mixtures of products, coming from metallation in the ortho position to the trifluoromethyl group and in the alpha position of the thiomethylic group, are obtained. In addition, products coming from substitution ortho,alpha to the thiomethyl group are also formed. All mono- and bimetallated intermediates showed to be good synthons for the synthesis of fluoro- and (trifluoromethyl)-substituted benzothiophenes and (trifluoromethyl)benzenes substituted on the thioalkylic chain and/or on the ring.
Electrophilic additions to allenes. VI. The role of steric versus electronic effects in the reactions of arenesulphenyl halides with allenes
Garratt, Dennis G.,Beaulieu, Pierre L.
, p. 2738 - 2744 (2007/10/02)
The role of steric and electronic effects during the rate and product determining steps for the addition of arenesulphenyl chlorides to 1,3-disubstituted allenes has been briefly examined.Both effects appear to be generally of minimal importance during the rate determinig step.The available rate data indicate the presence of little, if any, build up of positive charge on sulphur.These results are interpreted in terms of an SN2 attack on bivalent sulphur leading to an alkylidenethiiranium ion intermediate.Steric effects are of greater importance in the product determinig step, particularly when the sulphenyl chlorides possess two bulky ortho substituents, as in the case of 2,4,6-triisopropylbenzenesulphenyl chloride.
