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使用镁和锌-TMP碱对四硫富瓦烯进行选择性官能化:单、二、三、四取代衍生物的制备。

Selective Functionalization of Tetrathiafulvalene Using Mg- and Zn-TMP-Bases: Preparation of Mono-, Di-, Tri-, and Tetrasubstituted Derivatives.

作者信息

Nafe Julia, Auras Florian, Karaghiosoff Konstantin, Bein Thomas, Knochel Paul

机构信息

Department of Chemistry, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 München, Germany.

出版信息

Org Lett. 2015 Nov 6;17(21):5356-9. doi: 10.1021/acs.orglett.5b02715. Epub 2015 Oct 15.

Abstract

The tetrathiafulvalene-scaffold (TTF) reacts selectively in allylation, acylation, arylation, halogenation, and thiolation reactions via magnesium or zinc derivatives that are obtained by a direct metalation with Mg- and Zn-TMP-bases (TMP = 2,2,6,6-tetramethylpiperidyl). This stepwise functionalization provides access to a range of new mono-, di-, tri-, and tetra-functionalized TTF-derivatives and allows for fine-tuning of their energy levels.

摘要

四硫富瓦烯骨架(TTF)通过与Mg-TMP碱和Zn-TMP碱(TMP = 2,2,6,6-四甲基哌啶基)直接金属化得到的镁或锌衍生物,在烯丙基化、酰化、芳基化、卤化和硫醇化反应中选择性地发生反应。这种逐步功能化提供了获得一系列新的单官能、双官能、三官能和四官能TTF衍生物的途径,并允许对其能级进行微调。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e389/4797621/04b86b20fc06/ol-2015-027153_0003.jpg

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