Double C-H bond activation can enable an expeditious reaction pathway to cyclic compounds, offering an efficient tool to synthesize valuable molecules. However, cyclization reaction enabled by double C-H bond activation at one carbon atom is nearly unknown. Herein, we report a carbonylative formal cycloaddition of alkylarenes with imines via double benzylic C-H bond activation at one carbon atom, allowing a straightforward synthesis of β-lactams from readily accessible alkylarenes and imines, which paves the way for developing an annulation reaction through double C-H bond activation at one carbon atom.
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http://dx.doi.org/10.1021/jacs.3c00004 | DOI Listing |
Chem Sci
December 2024
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University Changchun Jilin 130012 China
The chemical recycling of polystyrene (PS) waste to value-added aromatic compounds is an attractive but formidable challenge due to the inertness of the C-C bonds in the polymer backbone. Here we develop a light-driven, copper-catalyzed protocol to achieve aerobic oxidation of various alkylarenes or real-life PS waste to benzoic acid and oxidized styrene oligomers. The resulting oligomers can be further transformed under heating conditions, thus achieving benzoic acid in up to 65% total yield through an integrated one-pot two-step procedure.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
University of Melbourne, School of Chemistry, 30 Flemington Rd., VIC 3095, Parkville, AUSTRALIA.
Palladium(II)-catalyzed C-H functionalization has attracted considerable attention as a pathway to late-stage modification of peptides. Herein, we report the Pd-catalyzed C(sp3)-H arylation of peptides directed by an amidoxime ether, which can be easily incorporated into peptides at any amide bond. Site- and stereoselective arylation of peptides has been achieved, including an unprecedented example of C-H arylation of an internal residue.
View Article and Find Full Text PDFAcc Chem Res
January 2025
Department of Chemistry and Chemistry Institution for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
ConspectusControlling selectivity through manipulation of reaction intermediates remains one of the most enduring challenges in organic chemistry, providing novel solutions for selective C-C π-bond functionalization. This approach, guided by activation principles, provides an effective method for selective functional group installation, enabling direct synthesis of organic molecules that are inaccessible through conventional pathways. In particular, the selective functionalization of N-conjugated allenes and alkynes has emerged as a promising research focus, driven by advances in controlling reactive intermediates and activation strategies.
View Article and Find Full Text PDFNat Commun
January 2025
Key Laboratory of advanced catalysis, College of Chemistry and Chemical Engineering, Lanzhou University, 730000, Lanzhou, China.
Nat Commun
January 2025
Department of Chemical and Biomolecular Engineering, National University of Singapore, Singapore, Republic of Singapore.
Employing electrochemistry for the selective functionalization of liquid alkanes allows for sustainable and efficient production of high-value chemicals. However, the large potentials required for C(sp)-H bond functionalization and low water solubility of such alkanes make it challenging. Here we discover that a Pt/IrO electrocatalyst with optimized Cl binding energy enables selective generation of Cl free radicals for C-H chlorination of alkanes.
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