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2‐Arylsilacyclobutane as a Latent Carbanion Reacting with CO 2
Author(s) -
Ishida Naoki,
Okumura Shintaro,
Kawasaki Tairin,
Murakami Masahiro
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201805333
Subject(s) - carbanion , carboxylation , chemistry , nucleophile , dimethylformamide , cleavage (geology) , carbon dioxide , nucleophilic addition , polar , photochemistry , bond cleavage , medicinal chemistry , organic chemistry , inorganic chemistry , catalysis , solvent , materials science , physics , astronomy , fracture (geology) , composite material
Abstract An electronically neutral 2‐arylsilacyclobutane generates a nucleophilic carbanion at room temperature through cleavage of the benzylic C−Si bond when simply dissolved in polar aprotic solvents such as N , N ‐dimethylformamide (DMF). The nucleophilic species is capable of capturing carbon dioxide to furnish a silalactone. The carboxylation reaction is unique in that no additional activating agents are required.