13575-00-3Relevant academic research and scientific papers
Synthesis of 4-aryl-and 4-acyl-1,3-dithiole-2-thiones via deprotonative zincation of 1,3-dithiole-2-thione
Otsuka, Shinya,Yorimitsu, Hideki
, (2018/09/10)
We have developed deprotonative zincation of 1,3-dithiole- 2- thione at the 4-position. Addition of lithium diisopropylamide to a THF solution of 1,3-dithiole- 2- thione containing ZnI2 and LiI generated the corresponding organozinc species. After this zincation, various aryl and acyl groups were installed at the 4-position by Pd-catalyzed cross-coupling reaction with aryl iodides and Cu-catalyzed acylation with acyl chlorides, respectively.
Selective Metalation of 1,3-Dithiole-2-thiones: An Effective Preparation of New Symmetrically and Nonsymmetrically Tetraarylated Tetrathiafulvalenes
Nafe, Julia,Knochel, Paul
, p. 103 - 114 (2015/12/26)
We report an efficient preparation of fully functionalized tetrathiafulvalene derivatives (TTF) with an extended π-system via a selective magnesiation of 1,3-dithiole-2-thiones (DTT) using 2,2,6,6-tetramethylpiperidin-1-ylmagnesium chloride-lithium chloride (TMPMgCl·LiCl); subsequent reaction with various electrophiles, such as halides, acid chlorides, allyl bromides, and aryl iodides, smoothly led to new mono- and difunctionalized 1,3-dithiole-2-thione derivatives. A triethyl phosphite mediated cross-coupling of the disubstituted 1,3-dithiole-2-thione derivatives with their oxygen analogues gave access to new symmetrically and nonsymmetrically tetraarylated tetrathiafulvalenes of interest as organic materials.
