Nickel-Catalyzed Cyclization/Carbonylation Reaction of -Allylbromoacetamides with Arylboronic Acids toward 2-Pyrrolidinones.

Org Lett

Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023 Dalian, Liaoning, People's Republic of China.

Published: January 2025

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A straightforward and efficient nickel-catalyzed cyclization/carbonylation transformation of -allylbromoacetamides toward the synthesis of 2-pyrrolidinone derivatives has been developed with arylboronic acids as the reaction partner. This transformation proceeds through a sequential single-electron-transfer pathway via 5-- cyclization and carbonyl insertion steps, furnishing a variety of 2-pyrrolidinone derivatives in good yields. Various useful functional groups were well tolerated. Moreover, formic acid is applied as the CO source here with nickel as the catalyst, which provides a good supplement for carbonylation chemistry and heterocycle synthesis.

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http://dx.doi.org/10.1021/acs.orglett.5c00003DOI Listing

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Nickel-Catalyzed Cyclization/Carbonylation Reaction of -Allylbromoacetamides with Arylboronic Acids toward 2-Pyrrolidinones.

Org Lett

January 2025

Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023 Dalian, Liaoning, People's Republic of China.

A straightforward and efficient nickel-catalyzed cyclization/carbonylation transformation of -allylbromoacetamides toward the synthesis of 2-pyrrolidinone derivatives has been developed with arylboronic acids as the reaction partner. This transformation proceeds through a sequential single-electron-transfer pathway via 5-- cyclization and carbonyl insertion steps, furnishing a variety of 2-pyrrolidinone derivatives in good yields. Various useful functional groups were well tolerated.

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