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A cobalt-catalyzed regioselective C-H halogenation methodology is reported herein. The highlight of this work is the highly selective C-H functionalization of anilides, which results in high-yielding, versatile, and practical halogenated products. Thereby, brominations, chlorinations and iodinations of many electron-rich and electron-deficient anilides were achieved in a highly selective fashion. Mechanistic studies with respect to the pathway of the reaction are also described.
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http://dx.doi.org/10.1039/c8ob01448e | DOI Listing |
Chem Commun (Camb)
September 2025
Center for Drug Research and Development, Guangdong Pharmaceutical University, Guangzhou, 510006, P. R. China.
Herein, we report an Ir(III)-catalyzed regioselective C-H acylmethylation of indolizines with β-ketosulfoxonium ylides, enabling the efficient synthesis of C3-functionalized indolizine derivatives. By modifying the reaction conditions, a controllable Ir(III)-catalyzed dicarbonylation of the same substrates was also achieved. In this transformation, β-ketosulfoxonium ylides serve as a rare alternative to conventional oxophenacyl halides.
View Article and Find Full Text PDFChem Sci
August 2025
College of Chemistry and Chemical Engineering, Jiangxi Province Engineering Research Center of Ecological Chemical Industry, Jiujiang University Jiujiang 332005 China
BN-fused aromatic compounds have garnered significant attention due to their unique electronic structures and exceptional photophysical properties, positioning them as highly promising candidates for applications in organic optoelectronics. However, the regioselective synthesis of BN isomers remains a formidable challenge, primarily stemming from the difficulty in precisely controlling reaction sites, limiting structural diversity and property tunability. Herein, we propose a regioselective synthetic strategy that employs 2,1-BN-naphthalene derivatives, wherein selective activation of N-H and C-H bonds is achieved in conjunction with -halogenated phenylboronic acids.
View Article and Find Full Text PDFJ Org Chem
September 2025
School of Chemistry and Chemical Engineering, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China.
Radical cascade cyclization of alkenes involving the insertion of sulfur dioxide has proven to be a promising tool to access sulfonylnated heterocycle compounds, whereas cyclization of unactivated alkenes has been much less explored. Here, we developed a three-component cascade of unactive alkenes with sulfur dioxide and aryldiazonium tetrafluoroborates to generate sulfonylated tetrahydropyridines and azepines via the cleavage of alkenyl C-H bonds. Moreover, this protocol exhibited excellent chemical and regioselectivity and compatibility with broad functional groups.
View Article and Find Full Text PDFJ Org Chem
August 2025
Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan.
Transformation of allylic C-H bonds into C-C bonds in a regioselective manner represents a powerful approach to generating complex molecules from simple starting materials. Herein, we report a protocol for net δ-C-H alkylation of allyl alcohols involving a sequential azo-ene reaction and an attendant Ni-catalyzed allylic substitution with Grignard reagents. This two-step strategy enables the regioselective alkylation of distal C-H bonds, a transformation that remains challenging via direct approaches under transition-metal catalysis.
View Article and Find Full Text PDFRSC Adv
August 2025
Department of Chemistry, Centre for Hydrogen Technology and Carbon Utilization (CeHy), Hindustan Institute of Technology and Science (HITS) Chennai 603103 India
In this work, we offer a method for selectively alkenylating C5-H and then annulating indole-4-carboxylic acid derivatives using ruthenium(ii) as a catalyst. Our approach facilitates the effective formation of fused lactone structures by employing a weakly coordinating carboxylic acid group at the C4 position as a guiding group. The reaction process starts with an alkenylation at the C5 position of the indole ring, followed by an intramolecular Michael addition to produce annulated lactones in high yields.
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