696-63-9Relevant articles and documents
Spontaneous substitution of azulene-derived benzylic alcohols by thiols and its application to labeling/protection of biothiols
Jin, Yu,Akagawa, Kengo,Kudo, Kazuaki
supporting information, (2021/02/27)
By mixing guaiazulene-3-methanol derivatives and thiols at room temperature, benzylic substitution of the alcohol proceeded to yield the corresponding sulfide. Because of the blue color of the guaiazulene derivative, this spontaneous reaction was used for labeling of paper-immobilized biothiols. By treatment with tris(2-carboxyethyl)phosphine hydrochloride, the guaiazulene-3-ylmethyl part of the sulfide could be removed and the original thiol recovered. Based on these findings, a guaiazulene-3-methanol derivative was used as a protective group for the synthesis of cysteine derivatives.
Copper-Catalyzed Direct Synthesis of Aryl Thiols from Aryl Iodides Using Sodium Sulfide Aided by Catalytic 1,2-Ethanedithiol
Xue, Hongyu,Jing, Bing,Liu, Shasha,Chae, Junghyun,Liu, Yajun
, p. 2272 - 2276 (2017/10/06)
A copper-catalyzed direct and effective synthesis of aryl thiols from aryl iodides using readily available Na 2 S·9H 2 O and 1,2-ethanedithiol was described. A variety of aryl thiols were readily obtained in yields of 76-99%. In this protocol, Na 2 S·9H 2 O was used as ultimate sulfur source, and 1,2-ethanedithiol functioned as an indispensable catalytic reagent.
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.