AI Article Synopsis
- The study presents a new method for photoredox carbobromination that allows the reaction of unactivated alkenes with α-bromocarbonyl compounds using blue LED light.
- It successfully utilizes various compounds like α-bromoesters and α-bromonitriles to produce alkylated alkenes from different types of alkenes, including terminal and disubstituted ones.
- The mechanism of this reaction follows a radical-addition radical-pairing (RARP) pathway, where the key step involves the interaction of bromine radicals and alkyl radicals instead of traditional carbocation mechanisms.
Article Abstract
We disclose a catalytic photoredox carbobromination of unactivated alkenes with α-bromocarbonyl compounds under a blue LED light. The reaction proceeds with α-bromoesters, α-bromonitriles and α-bromo-γ-lactones along with terminal and 1,2-disubstituted internal alkenes. Reactions with indenes and 1,1-disubstituted alkenes generate alkylated alkenes. Mechanistic studies by product selectivity and three-way competitive crossover experiments suggest that the reaction operates by a radical-addition radical-pairing (RARP) mechanism. The catalytic turnover is achieved by a single electron reduction of PC by Br (or Br ), rather than by alkyl radical (R•), and the product is generated by the pairing of Br• (or Br•) and R•, instead of the combination of Br and a carbocation (R).
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11694795 | PMC |
| http://dx.doi.org/10.1021/acscatal.4c00955 | DOI Listing |
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Article Synopsis
- The study presents a new method for photoredox carbobromination that allows the reaction of unactivated alkenes with α-bromocarbonyl compounds using blue LED light.
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