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

Abstract : 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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-03137415
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Submitted on : Monday, February 22, 2021 - 10:35:03 AM
Last modification on : Wednesday, April 7, 2021 - 3:18:14 PM
Long-term archiving on: : Sunday, May 23, 2021 - 6:21:15 PM

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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, Royal Society of Chemistry, 2021, 8 (3), pp.514-521. ⟨10.1039/D0QO01031F⟩. ⟨hal-03137415⟩

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