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- Title
Electroreductive alkylations of (hetero)arenes with carboxylic acids.
- Authors
Wang, Bing; Huang, Xianshuai; Bi, Huihua; Liu, Jie
- Abstract
Carboxylic acids are widely available and generally inexpensive from abundant biomass feedstocks, and they are suitable and generic coupling partners in synthetic chemistry. Reported herein is an electroreductive coupling of stable and versatile carboxylic acids with (hetero)arenes using protons as the hydrogen source. The application of an earth-abundant titanium catalyst has significantly improved the deoxygenative reduction process. Preliminary mechanistic studies provide insights into the deoxygenative reduction of in-situ generated ketone pathway, and the intermediacy generation of ketyl radical and alkylidene titanocene. Without the necessity of pressurized hydrogen or stoichiometric hydride as reductants, this protocol enables highly selective and straightforward synthesis of various functionalized and structurally diverse alkylbenzenes under mild conditions. The utility of this reaction is further demonstrated through practical and valuable isotope incorporation from readily available deuterium source. Carboxylic acids are excellent theoretical candidates for alkylation reactions given their low cost and high availability as products from traditional and also modern feedstock derivatization reactions. Here the authors use simple carboxylic acids to functionalize the C–H bonds of electron-rich arenes under electroreductive conditions with a titanium catalyst.
- Subjects
CARBOXYLIC acids; TITANIUM catalysts; BIOMASS chemicals; AROMATIC compounds; KETONES; ALKYLATION
- Publication
Nature Communications, 2024, Vol 15, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-024-49355-1