2037-31-2Relevant articles and documents
SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF
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Paragraph 0032; 0033; 0063; 0067; 0069; 0070, (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.
Kinetics and mechanism of the aminolysis of thiophenyl methylacetates in acetonitrile
Oh, Hyuck Keun,Yang, Jin Hee,Cho, In Ho,Lee, Hai Whang,Lee, Ikchoon
, p. 485 - 490 (2007/10/03)
The aminolysis of Z-thiophenyl methylacetates (C2H5C(double bond O)SC6H4Z) with X-benzylamines in acetonitrile has been investigated at 45 °C. The reaction is found to proceed by a stepwise mechanism in which the rate-determining step is the breakdown of the zwitterionic tetrahedral intermediate, T±, with possibly a hydrogen-bonded four-center-type transition state. These mechanistic conclusions are drawn based on (i) the large magnitude of βX (= 1.2 to approximately 2.5) and βz (= -0.9 to approximately -1.5), (ii) the normal kinetic isotope effects (kH/kD?1.2) involving deuterated benzylamines (XC6H4CH2ND2), (iii) a large positive ρxz (= 2.4) and (iv) adherence to the reactivity-selectivity principle in all cases. The extremely large βX (βnuc) values can be accounted for by the loss of a strong localized cationic charge on the N atom of benzylamines in the expulsion from the T±. The pKa° (≥10.0) is high due to a large ratio of the expulsion rates of the amine (k-a) to thiophenolate (kb) (k-a/kb) from the T±.
