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Synthesis 2021; 53(24): 4662-4671
DOI: 10.1055/a-1559-3384
paper

Regioselective Iodine/Zinc Exchange for the Selective Functionalization of Polyiodinated Arenes and Heterocycles in Toluene

Florian Sanchez‡
,
Alexandre Desaintjean‡
,
Fanny Danton
,
Paul Knochel  ∗
We thank the Deutsche Forschungsgemeinschaft (DFG) and Ludwig-Maximilians-Universität München for financial support.
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Abstract

Regioselective I/Zn-exchange reactions were performed on polyiodinated arenes or heterocycles within 20 minutes at 0–25 °C using the bimetallic combination pTol2Zn·2LiOR [R = (CH2)2N(Me)(CH2)2NMe2] in toluene. The resulting diaryl- or diheteroarylzincs reacted well with allylic bromides and acyl chlorides to provide functionalized (hetero)aryl iodides in good yields.

Key words

alkoxides - apolar solvents - arenes - heterocycles - lithium - regioselective iodine/zinc exchange - zinc

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1559-3384.
  • Supporting Information


Publication History

Received: 05 July 2021

Accepted after revision: 27 July 2021

Accepted Manuscript online:
27 July 2021

Article published online:
24 August 2021

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