Work

Alcohol imination catalyzed by carbon nanostructures synthesized by C(sp2)-C(sp3) free radical coupling

Year: 2023

Type: article

Abstract: Imines are important intermediates for synthesizing various fine chemicals, with the disadvantage of requiring the use of expensive metal-containing catalysts. We report that the dehydrogenative cross-coupling of phenylmethanol and benzylamine (or aniline) directly forms the corresponding imine with a yield of up to 98%, and water as the sole by-product, in the presence of a stoichiometric base, using carbon nanostructures as the "green" metal-free carbon catalysts with high spin concentrations, which is synthesized by C(sp 2 )-C(sp 3 ) free radical coupling reactions. The catalytic mechanism is attributed to the unpaired electrons of carbon catalysts to reduce O 2 to O 2 ·− , which triggers the oxidative coupling reaction to form imines, whereas the holes in the carbon catalysts receive electrons from the amine to restore the spin states. This is supported by density functional theory calculations. This work will open up an avenue for synthesizing carbon catalysts and offer great potential for industrial applications.

Source: iScience

DOI: 10.1016/j.isci.2023.106659

Authors: Cheng Wang, Zirui Qiao, Yulan Tian, Haijun Yang, Huaqiang Cao, Anthony K. Cheetham

Institutions: Tsinghua University, University of California, Santa Barbara

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,150