Alkenes as hydrogen trappers to control the regio-selective ruthenium( ii ) catalyzed ortho C–H silylation of amides and anilides

Qiao Lin (1) , Zirui Lin (1) , Mingxing Pan (1) , Qiaojin Zheng (1) , Hui Li (1) , Xiuwen Chen (1) , Christophe Darcel (2) , Pierre H. Dixneuf (2) , Bin Li (1)

1 Wuyi University
2 ISCR - Institut des Sciences Chimiques de Rennes

A convenient and practical pathway to versatile silylated amides and anilides is described via efficient and selective ruthenium( ii ) catalyzed ortho C–H silylation with different alkenes as the hydrogen acceptors. , A convenient and practical pathway to versatile silylated amides and anilides is described via efficient and selective ruthenium( ii ) catalyzed ortho C–H silylation. Both amides and anilides were successfully silylated with good functional group tolerance and high regioselectivity. Different alkenes as the hydrogen acceptors played a crucial role in these two catalytic systems. Unexpectedly, two pathways for RuHCl(CO)(PPh 3 ) 2 /KOAc catalyzed C–H silylation involving a 5-membered ruthenacycle with arylamides and a 6-membered ruthenacycle with arylanilides, take place depending on the nature of the alkene as the hydrogen trapper.

Domaines: Chimie; Chimie organique

Qiao Lin, Zirui Lin, Mingxing Pan, Qiaojin Zheng, Hui Li, et al.. Alkenes as hydrogen trappers to control the regio-selective ruthenium( ii ) catalyzed ortho C–H silylation of amides and anilides. Organic Chemistry Frontiers, 2021, 8 (3), pp.514-521. ⟨10.1039/D0QO01031F⟩. ⟨hal-03137415⟩