Examples of air-and water-stable main-group radicals are scarce in the literature due to the higher reactivity of radical compounds as well as several synthetic challenges. Herein, we report two stable structurally characterized glyoxal radical cations (1(center dot+) and 2(center dot+)) stabilized by cyclic(alkyl)(amino)carbene (CAAC) and bicyclic (alkyl)(amino)carbene (BICAAC), respectively. Both 1(center dot+) and 2(center dot+) are stable under harsh conditions such as strong acids, bases, mild oxidizing agents, and reducing agents, as well as towards bovine serum. Radical (2(center dot+)) represents the first isolated radical stabilized by a BICAAC ligand.
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Univ Calif San Diego, UCSD CNRS Joint Res Chem Lab IRL 3555, Dept Chem & Biochem, La Jolla, CA 92093 USA
Univ Rennes, ISCR, Ecole Natl Super Chim Rennes, CNRS,UMR 6226, F-35000 Rennes, FranceUniv Calif San Diego, UCSD CNRS Joint Res Chem Lab IRL 3555, Dept Chem & Biochem, La Jolla, CA 92093 USA
Lorkowski, Jan
Serrato, Melinda R.
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Univ Calif San Diego, UCSD CNRS Joint Res Chem Lab IRL 3555, Dept Chem & Biochem, La Jolla, CA 92093 USAUniv Calif San Diego, UCSD CNRS Joint Res Chem Lab IRL 3555, Dept Chem & Biochem, La Jolla, CA 92093 USA
Serrato, Melinda R.
Gembicki, Milan
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Univ Calif San Diego, UCSD CNRS Joint Res Chem Lab IRL 3555, Dept Chem & Biochem, La Jolla, CA 92093 USAUniv Calif San Diego, UCSD CNRS Joint Res Chem Lab IRL 3555, Dept Chem & Biochem, La Jolla, CA 92093 USA
Gembicki, Milan
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Mauduit, Marc
Bertrand, Guy
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Univ Calif San Diego, UCSD CNRS Joint Res Chem Lab IRL 3555, Dept Chem & Biochem, La Jolla, CA 92093 USAUniv Calif San Diego, UCSD CNRS Joint Res Chem Lab IRL 3555, Dept Chem & Biochem, La Jolla, CA 92093 USA
Bertrand, Guy
Jazzar, Rodolphe
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Univ Calif San Diego, UCSD CNRS Joint Res Chem Lab IRL 3555, Dept Chem & Biochem, La Jolla, CA 92093 USAUniv Calif San Diego, UCSD CNRS Joint Res Chem Lab IRL 3555, Dept Chem & Biochem, La Jolla, CA 92093 USA
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Univ Calif San Diego, CNRS, Dept Chem & Biochem, Joint Res Lab,UMI 3555, La Jolla, CA 92093 USAUniv Calif San Diego, CNRS, Dept Chem & Biochem, Joint Res Lab,UMI 3555, La Jolla, CA 92093 USA
Jazzar, Rodolphe
Soleilhavoup, Michele
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Univ Calif San Diego, CNRS, Dept Chem & Biochem, Joint Res Lab,UMI 3555, La Jolla, CA 92093 USAUniv Calif San Diego, CNRS, Dept Chem & Biochem, Joint Res Lab,UMI 3555, La Jolla, CA 92093 USA
Soleilhavoup, Michele
Bertrand, Guy
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Univ Calif San Diego, CNRS, Dept Chem & Biochem, Joint Res Lab,UMI 3555, La Jolla, CA 92093 USAUniv Calif San Diego, CNRS, Dept Chem & Biochem, Joint Res Lab,UMI 3555, La Jolla, CA 92093 USA