Csp2-N Bond Formation via Ligand-Free Pd-Catalyzed Oxidative Coupling Reaction of N-Tosylhydrazones and Indole Derivatives

Maxime Roche (1) , Gilles Frison (2) , Jean-Daniel Brion (1) , Olivier Provot (1) , Abdallah Hamze (1) , Mouâd Alami (1)

1 MBCIS - Molécules bioactives, conception, isolement et synthèse
2 DCMR - Laboratoire des mécanismes réactionnels

In a fresh approach to the synthesis of N-vinylazoles, a ligand-free palladium catalytic system was found to promote the Csp2-N bond-forming reaction utilizing N-tosylhydrazones and N-H azoles. This process shows functional group tolerance, di-, tri- and tetrasubstituted N-vinylazoles were obtained in high yields. Under the optimized conditions, the reaction proceeds with high stereoselectivity depending on the nature of the coupling partners

Domaines: Catalyse; Chimie organique

Maxime Roche, Gilles Frison, Jean-Daniel Brion, Olivier Provot, Abdallah Hamze, et al.. Csp2-N Bond Formation via Ligand-Free Pd-Catalyzed Oxidative Coupling Reaction of N-Tosylhydrazones and Indole Derivatives. Journal of Organic Chemistry, 2013, 78, pp.8485-8495. ⟨10.1021/jo401217x⟩. ⟨hal-00849710⟩