Golden Face of Phosphine: Cascade Reaction to Bridgehead Methanophosphocines by Intramolecular Double Hydroarylation

Rachida Babouri (1) , Lanciné Traore (1) , Yves-Alain Bekro (2) , Victoria Matveeva (3) , Yulia Sadykova (3) , Julia Voronina (3) , Alexander Burilov (3) , Tahar Ayad (4) , Jean-Noël Volle (1) , David Null Virieux (1) , Jean-Luc Pirat (1)

1 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 LCBOSN
3 IOPC - A.E. Arbuzov Institute of Organic and Physical Chemistry
4 SSOPN - Synthèses sélective organique et produits naturels

Reported herein is the first example of a gold-catalyzed cyclization of bis(arylmethyl)ethynylphosphine oxides. This represents an original approach to bridgehead methanophosphocines 1, eight-membered heterocycles. Gold catalyst in combination with triflic acid activates alkyne and induces a double hydroarylation. Mechanistic studies suggest that the reaction proceeds stepwise, forming first the 1H-isophosphinoline 2-oxide 5. Reduction and protection of the corresponding phosphine oxides 1 described herein also highlight the effectiveness of our approach to this new class of electron-rich ligands.

Domaines: Chimie organique

Rachida Babouri, Lanciné Traore, Yves-Alain Bekro, Victoria Matveeva, Yulia Sadykova, et al.. Golden Face of Phosphine: Cascade Reaction to Bridgehead Methanophosphocines by Intramolecular Double Hydroarylation. Organic Letters, 2019, 21 (1), pp.45-49. ⟨10.1021/acs.orglett.8b03474⟩. ⟨hal-01985208⟩