Literature DB >> 28035825

Selective Metalations of 1,4-Dithiins and Condensed Analogues Using TMP-Magnesium and -Zinc Bases.

Alicia Castelló-Micó1, Julia Nafe1, Kosuke Higashida1, Konstantin Karaghiosoff1, Marc Gingras2, Paul Knochel1.   

Abstract

TMPMgCl·LiCl and TMPZnCl·LiCl allow facile magnesiation and zincation, respectively, of the 1,4-dithiin scaffold, producing polyfunctionalized 1,4-dithiins. A subsequent metalation of these S-heterocycles can also be achieved with the same TMP bases, leading to 2,3-disubstituted-1,4-dithiins. The Mg- and Zn-TMP bases allow as well the successful metalation of 1,4,5,8-tetrathianaphthalene and 1,4,5,6,9,10-hexathiaanthracene.

Entities:  

Year:  2016        PMID: 28035825     DOI: 10.1021/acs.orglett.6b03539

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  Regioselective Magnesiation and Zincation Reactions of Aromatics and Heterocycles Triggered by Lewis Acids.

Authors:  Alexander Kremsmair; Andreas Hess; Benjamin Heinz; Paul Knochel
Journal:  Chemistry       Date:  2021-11-29       Impact factor: 5.020

2.  A Predictive Model Towards Site-Selective Metalations of Functionalized Heterocycles, Arenes, Olefins, and Alkanes using TMPZnCl⋅LiCl.

Authors:  Moritz Balkenhohl; Harish Jangra; Ilya S Makarov; Shu-Mei Yang; Hendrik Zipse; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-08       Impact factor: 16.823

  2 in total

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