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A Giese Reaction for Electron-Rich Alkenes

preprint
submitted on 08.11.2020, 20:25 and posted on 10.11.2020, 07:23 by Qi Huang, Sankar Rao Suravarapu, Philippe Renaud
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.

Funding

The Swiss National Science Foundation (Project 200020_172621)

History

Email Address of Submitting Author

philippe.renaud@dcb.unibe.ch

Institution

University of Bern

Country

Switzerland

ORCID For Submitting Author

0000-0002-9069-7109

Declaration of Conflict of Interest

None

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