Issue 6, 2021

A Giese reaction for electron-rich alkenes


A general method for the hydroalkylation of electron-rich terminal and non-terminal alkenes such as enol esters, alkenyl sulfides, enol ethers, silyl enol ethers, enamides and enecarbamates has been developed. The reactions are carried out at room temperature under air initiation in the presence of triethylborane acting as a chain transfer reagent and 4-tert-butylcatechol (TBC) as a source of hydrogen atom. The efficacy of the reaction is best explained by very favorable polar effects supporting the chain process and minimizing undesired polar reactions. The stereoselective hydroalkylation of chiral N-(alk-1-en-1-yl)oxazolidin-2-ones takes place with good to excellent diastereocontrol.

Graphical abstract: A Giese reaction for electron-rich alkenes

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Article information

Article type
Edge Article
18 Nov 2020
17 Dec 2020
First published
17 Dec 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 2225-2230

A Giese reaction for electron-rich alkenes

Q. Huang, S. R. Suravarapu and P. Renaud, Chem. Sci., 2021, 12, 2225 DOI: 10.1039/D0SC06341J

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