An Electrophilic Ruthenium Complex that Enables the Cycloisomerization of 1,6‐Enynes to Access Azabicyclo[4.1.0]heptenes

Rui Liu (1) , Dongfeng Yang (1) , Fengwei Chang (1) , Laurent Giordano (2) , Guohua Liu (1) , Alphonse Tenaglia (2)

1 SHNU - Shanghai Normal University
2 ISM2 - Institut des Sciences Moléculaires de Marseille

Cycloisomerization of 1,6‐enynes to access azabicyclo[4.1.0]heptenes was achieved in the presence of commercially available [RuCl2(CO)3]2 after a comprehensive study on the electronic properties of ruthenium complexes. A series of 1,6‐enynes bearing an internal/terminal alkyne motif proved to be good candidates for substrates, giving their corresponding bicyclo[4.1.0]heptenes in good to excellent yields. Substitution patterns on either alkyne or alkene have no significant influence on the yields of bicyclic adducts.

Domaines: Chimie organique; Catalyse

Rui Liu, Dongfeng Yang, Fengwei Chang, Laurent Giordano, Guohua Liu, et al.. An Electrophilic Ruthenium Complex that Enables the Cycloisomerization of 1,6‐Enynes to Access Azabicyclo[4.1.0]heptenes. Asian Journal of Organic Chemistry, 2019, 8 (11), pp.2011-2016. ⟨10.1002/ajoc.201900529⟩. ⟨hal-02514511⟩