Cu(II) carboxylate arene C─H functionalization: Tuning for nonradical pathways.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 36001664.
- Also identified by DOI 10.1126/sciadv.add1594 and PMC identifier 9401614.
- Licence recorded as CC BY-NC.
- Because redistribution is not established, this page shows the abstract only. Follow the links below for the full text.
Abstract
We report carbon-hydrogen acetoxylation of nondirected arenes benzene and toluene, as well as related functionalization with pivalate and 2-ethylhexanoate ester groups, using simple copper(II) [Cu(II)] salts with over 80% yield. By changing the ratio of benzene and Cu(II) salts, 2.4% conversion of benzene can be reached. Combined experimental and computational studies results indicate that the arene carbon-hydrogen functionalization likely occurs by a nonradical Cu(II)-mediated organometallic pathway. The Cu(II) salts used in the reaction can be isolated, recycled, and reused with little change in reactivity. In addition, the Cu(II) salts can be regenerated in situ using oxygen and, after the removal of the generated water, the arene carbon-hydrogen acetoxylation and related esterification reactions can be continued, which leads to a process that enables recycling of Cu(II).