Iron-Catalyzed Cross-Coupling of Functionalized Benzylmanganese Halides with Alkenyl Iodides, Bromides, and Triflates

Alexandre Desaintjean (1) , Sophia Belrhomari (1) , Lidie Rousseau (2, 3) , Guillaume Lefèvre (3) , Paul Knochel (1)

1 Department of Chemistry [München]
2 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)
3 CSB2D - Catalysis, Synthesis of Biomolecules and Sustainable Development

Various substituted benzylic manganese chlorides were prepared by insertion of magnesium turnings in the presence of MnCl2·2LiCl in THF at −5 °C within 2 h. These benzylic manganese reagents underwent smooth cross-couplings with various functionalized alkenyl iodides, bromides, and triflates or iodoacrylates in the presence of 10 mol % FeCl2 at 25 °C for 1–12 h. Mechanistic studies showed that benzylic manganese halides produced, in the presence of FeCl2, a very reactive iron ate complex.

Domains: Organic chemistry; Catalysis

Alexandre Desaintjean, Sophia Belrhomari, Lidie Rousseau, Guillaume Lefèvre, Paul Knochel. Iron-Catalyzed Cross-Coupling of Functionalized Benzylmanganese Halides with Alkenyl Iodides, Bromides, and Triflates. Organic Letters, 2019, 21, pp.8684-8688. ⟨10.1021/acs.orglett.9b03292⟩. ⟨cea-02321208⟩