AI Article Synopsis
- A new catalytic method using N-Heterocyclic carbenes has been created for adding trichloromethyl and acyl groups to alkenes, utilizing tetrachloromethane and aldehydes.
- The process involves a single electron transfer step, converting a Breslow intermediate's enolate form to a ketyl radical and a temporary trichloromethyl radical.
- This results in the trichloromethyl radical reacting with the alkene, with the alkyl radical favorably being captured by the ketyl radical, yielding a product through atom transfer radical addition.
Article Abstract
N-Heterocyclic carbene catalysis enabling vicinal trichloromethylacylation of alkenes using tetrachloromethane and aldehydes has been developed. The reaction involves single electron transfer from the enolate form of the Breslow intermediate to tetrachloromethane to generate the persistent Breslow intermediate-derived ketyl radical and a transient trichloromethyl radical. After radical addition of the trichloromethyl radical to an alkene, the prolonged alkyl radical is preferentially captured by the ketyl radical over tetrachloromethane leading to the atom transfer radical addition product.
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| http://dx.doi.org/10.1021/acs.orglett.1c02639 | DOI Listing |
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