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Umpolung Reactivity of Aldehydes toward Carbon Dioxide
Author(s) -
Juhl Martin,
Lee JiWoong
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201806569
Subject(s) - carboxylation , umpolung , chemistry , carbon dioxide , reactivity (psychology) , reagent , catalysis , cyanohydrin , organic chemistry , combinatorial chemistry , supercritical carbon dioxide , electrochemical reduction of carbon dioxide , carbon monoxide , nucleophile , medicine , alternative medicine , pathology
Carbon dioxide is an intrinsically stable molecule. Therefore, its activation requires extra energy input in the form of reactive reagents and/or activated catalysts and, often, harsh reaction conditions. Reported here is a direct carboxylation reaction of aromatic aldehydes with carbon dioxide to afford α‐keto acids as added‐value products. In situ generation of a reactive cyanohydrin was the key to the successful carboxylation reaction under operationally mild reaction conditions (25–40 °C, 1 atm CO 2 ). The resulting α‐keto acids served as a platform for α‐amino acid synthesis by reductive amination reactions, illustrating the chemical synthesis of essential bioactive molecules from carbon dioxide.