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Synthesis 2016; 48(01): 103-114
DOI: 10.1055/s-0035-1560728
DOI: 10.1055/s-0035-1560728
paper
Selective Metalation of 1,3-Dithiole-2-thiones: An Effective Preparation of New Symmetrically and Nonsymmetrically Tetraarylated Tetrathiafulvalenes
Further Information
Publication History
Received: 17 September 2015
Accepted after revision: 22 September 2015
Publication Date:
21 October 2015 (online)
Abstract
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560728.
- Supporting Information
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