Transition-metal-catalyzed lactamization and lactonization of C-H bonds with CO assisted by the chelation of amino or hydroxyl groups have been developed but limited to the use of precious metal catalysts such as palladium and rhodium. In this work, we report the nonprecious metal nickel-catalyzed lactamization reaction of 2-arylanilines with CO under redox-neutral conditions via C-H bond activation. The reaction displayed excellent functional group tolerance, providing various phenanthridinones with moderate to high yields.
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http://dx.doi.org/10.1021/acs.orglett.4c01156 | DOI Listing |
Org Lett
July 2024
Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada.
An intermolecular nickel-catalyzed reductive 1,2-alkylarylation of acrylates with cyclopropylamine NHP esters and aryl iodides is reported. This operationally simple protocol provides direct access to 1-alkylcyclopropylamine scaffolds. The mild conditions are compatible with four-membered α-amino strained rings as well as five- and six-membered ring systems.
View Article and Find Full Text PDFChemistry
August 2024
Dipartimento di Chimica "Giacomo Ciamician", Alma Mater Studiorum-Università di Bologna, via P. Gobetti 85, 40129, Bologna, Italy.
A new nickel catalyzed cross-electrophile coupling for accessing γ-lactams (isoindolinones) as well as γ-lactones (isobenzofuranones) via carbonylation with CO is documented. The protocol exploits the synergistic role of redox-active Ni(II) complexes and AlCl as a CO activator/oxygen scavenger, leading to the formation of a wide range of cyclic amides and esters (28 examples) in good to high yields (up to 87 %). A dedicated computational investigation revealed the multiple roles played by AlCl.
View Article and Find Full Text PDFOrg Lett
May 2024
State Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Transition-metal-catalyzed lactamization and lactonization of C-H bonds with CO assisted by the chelation of amino or hydroxyl groups have been developed but limited to the use of precious metal catalysts such as palladium and rhodium. In this work, we report the nonprecious metal nickel-catalyzed lactamization reaction of 2-arylanilines with CO under redox-neutral conditions via C-H bond activation. The reaction displayed excellent functional group tolerance, providing various phenanthridinones with moderate to high yields.
View Article and Find Full Text PDFJ Org Chem
November 2024
Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
Herein, we report a single-step, multicomponent approach to versatile γ-lactams through dual photoredox/nickel-catalyzed dicarbofunctionalization of α,β-unsaturated γ-butyrolactam. This reaction utilized alkyl trimethylgermanium as a radical precursor and acyl chloride as the electrophile, demonstrating remarkable functional group compatibility.
View Article and Find Full Text PDFJ Org Chem
January 2024
Department of Chemistry, Chonnam National University, Gwangju 61186, Republic of Korea.
We successfully developed a nickel-catalyzed transamidation method for the ring opening of -acyl lactams. The method involves a reaction between -benzoylpyrrolidin-2-one derivatives and aniline derivatives, with Ni(PPh)Cl serving as the catalyst, 2,2'-bipyridine as the ligand, and manganese as the reducing agent. This reaction led to the formation of ring-opening-amidated products in good yields.
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