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

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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. 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)(PPh3)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.

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

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Article information


Submitted
03 Sep 2020
Accepted
04 Oct 2020
First published
10 Oct 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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

Q. Lin, Z. Lin, M. Pan, Q. Zheng, H. Li, X. Chen, C. Darcel, P. H. Dixneuf and B. Li, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO01031F

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