Repurposing Aryl Boronic Acids as Halogen‐Atom Transfer Agents

European Journal of Organic Chemistry, vol. 29

Abstract

Halogen‐atom transfer (XAT) is an important method for the generation of carbon radicals. Hence, the development of new XAT agents has emerged as an important research avenue in organic synthesis. Aryl radicals are particularly promising XAT agents but have witnessed limited application. Herein, we introduce a protocol that repurposes widely available aryl boronic acids as XAT agents for alkyl iodide activation. We exemplify this concept on a Giese reaction, constructing valuable, sp 3 ‐rich scaffolds. The reaction is highly efficient and tolerant of a variety of sensitive functional groups. Furthermore, we showcase the compatibility of our boronic acid XAT agents in processes based on the use of transition metals, like cobalt for desaturative purposes.

Authors 3

1. Daigo Hayashi Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Aachen Germany

2. Thomas Sephton corresponding Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Aachen Germany

3. Daniele Leonori corresponding Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Aachen Germany