Synlett 2024; 35(04): 431-436
DOI: 10.1055/a-2106-1678
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11th Singapore International Chemistry Conference (SICC-11)

Regiodivergent Synthesis of Brominated Pyridylthiophenes by Overriding the Inherent Substrate Bias

Masahiro Hosoya
a   Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan
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a   Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan
b   Research Center for Membrane and Film Technology, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan
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a   Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan
› Institutsangaben

This work was supported by JSPS KAKENHI (JP19H02717) and Hyogo Science and Technology Association. This work was performed under the Cooperative Research Program of the Network Joint Research Center for Materials and Devices.


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Abstract

A regiocontrolled functionalization of a pyridylthiophene scaffold was accomplished. Regioselectivity for deprotonation of the pyridylthiophene was switched by changing the reaction conditions, including the metal amide base and the solvent. Subsequently, in situ transmetalation and halogen dance on the corresponding organometallic species were controlled by additives and the reaction temperature, as well as by the above reaction conditions. This method successfully enabled the synthesis of four iodinated constitutional isomers from a single starting material, 2-(5-bromo-2-thienyl)pyridine.

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Publikationsverlauf

Eingereicht: 14. Mai 2023

Angenommen nach Revision: 05. Juni 2023

Accepted Manuscript online:
05. Juni 2023

Artikel online veröffentlicht:
24. Juli 2023

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