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.5c00003 | DOI Listing |
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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September 2024
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
The Narasaka-Heck reaction is one of the most straightforward methods for constructing pyrroline derivatives. Herein, we report a novel nickel-catalyzed three-component carbonylation reaction, which cleverly realizes the continuous construction of C(sp)-N bonds and C(sp)-C(sp) bonds and effectively promotes the synthesis of acyl-substituted pyrroline derivatives. Furthermore, this strategy not only expands the conversion pathway of γ,δ-unsaturated oxime esters but also provides a new method for the synthesis of nitrogen-containing heterocyclic compounds.
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