Synthesis 2023; 55(12): 1855-1862
DOI: 10.1055/a-2012-5078
paper
Special Issue dedicated to Prof. Alain Krief

Visible-Light-Mediated Germanylation of Aryl Fluorides: Synthetic and Mechanistic Insights

Valentin Magné
a   CNRS/Université Paul Sabatier, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR5069), 118 Route de Narbonne, 31062 Toulouse Cedex 09, France
,
Corentin Bellanger
a   CNRS/Université Paul Sabatier, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR5069), 118 Route de Narbonne, 31062 Toulouse Cedex 09, France
,
b   Department of Biomedical Science, College of Science, Komar University of Science and Technology, 46001 Sulaymaniyah, Kurdistan Region, Iraq
,
Nathalie Saffon-Merceron
c   Institut de Chimie de Toulouse (UAR 2599), 118 Route de Narbonne, 31062 Toulouse Cedex 09, France
,
Sami Lakhdar
a   CNRS/Université Paul Sabatier, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR5069), 118 Route de Narbonne, 31062 Toulouse Cedex 09, France
› Author Affiliations
The Centre National de la Recherche Scientifique (CNRS), the Université Paul Sabatier (UPS), and the Agence Nationale de la Recherche (ANR – 220087, MLC-PhotoPhos) are gratefully acknowledged for financial support of this work.


Dedicated to Prof. Alain Krief on the occasion of his 80th birthday.

Abstract

We describe herein a metal-free synthesis of aryltriphenylgermanes from the reaction of triphenylgermane with fluoro(hetero)arenes in the presence of a base under blue light irradiation. The reaction proceeds under mild conditions and tolerates a few functionalities. The scope and limitations of this unprecedented approach are analyzed based on preliminary mechanistic studies.

Supporting Information



Publication History

Received: 28 November 2022

Accepted after revision: 13 January 2023

Accepted Manuscript online:
13 January 2023

Article published online:
13 February 2023

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