A Selective C-C Bond Cleavage Strategy Promoted by Visible Light.

Rafael D C Gallo Marcelo Duarte Amanda Dantas SilvaCelso Y OkadaVictor M Deflon Igor D Jurberg

Published in: Organic letters (2021)

A new visible-light-promoted reaction between aryldiazoacetates and 1,3-diketones allows good yields and selectivities for C-C bond insertions, leading to the corresponding 1,4-dicarbonyl compounds. This transformation is straightforward and highly practical. It tolerates air and moisture and does not require the use of any metals. Mechanistic investigations support the involvement of a key cyclopropanol intermediate derived from an intramolecular rearrangement.

Keyphrases

visible light
electron transfer
transition metal
health risk
human health
dna binding
risk assessment
transcription factor
heavy metals