Diacids
are important monomers in the polymer industry to construct
valuable materials. Dicarboxylation of unsaturated bonds, such as
alkenes and alkynes, with CO2 has been demonstrated as
a promising synthetic method. However, dicarboxylation of CC
single bonds with CO2 has rarely been investigated. Herein
we report a novel electrochemical ring-opening dicarboxylation of
CC single bonds in strained rings with CO2. Structurally
diverse glutaric acid and adipic acid derivatives were synthesized
from substituted cyclopropanes and cyclobutanes in moderate to high
yields. In contrast to oxidative ring openings, this is also the first
realization of an electroreductive ring-opening reaction of strained
rings, including commercialized ones. Control experiments suggested
that radical anions and carbanions might be the key intermediates
in this reaction. Moreover, this process features high step and atom
economy, mild reaction conditions (1 atm, room temperature), good
chemoselectivity and functional group tolerance, low electrolyte concentration,
and easy derivatization of the products. Furthermore, we conducted
polymerization of the corresponding diesters with diols to obtain
a potential UV-shielding material with a self-healing function and
a fluorine-containing polyester, whose performance tests showed promising
applications.