Herein, a copper-catalyzed intermolecular [4+1] spiroannulation of indoles with alkynyldiazoketones affording various indole-based spirocyclic molecules a chemoselective C-H functionalization/dearomatization sequence was developed.
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Copper-catalyzed chemoselective C-H functionalization/dearomatization sequence: direct access to indole-based spirocyclic scaffolds.
Chem Commun (Camb)
March 2025
School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road Shanghai, 200241, P. R. China.
Herein, a copper-catalyzed intermolecular [4+1] spiroannulation of indoles with alkynyldiazoketones affording various indole-based spirocyclic molecules a chemoselective C-H functionalization/dearomatization sequence was developed.
View Article and Find Full Text PDFChemoselective Functionalization of Tertiary C-H Bonds of Allylic Ethers: Enantioconvergent Access to sec,tert-Vicinal Diols.
Angew Chem Int Ed Engl
February 2025
School of Chemistry, Dalian University of Technology, 116024, Dalian, China.
While enantioenriched alcohols are highly significant in medicinal chemistry, total synthesis, and materials science, the stereoselective synthesis of tertiary alcohols with two adjacent stereocenters remains a formidable challenge. In this study, we present a dual catalysis approach utilizing photoredox and nickel catalysts to enable the unprecedented chemoselective functionalization of tertiary allylic C-H bonds in allyl ethers instead of cleaving the C-O bond. The resulting allyl-Ni intermediates can undergo coupling with various aldehydes, facilitating a novel enantioconvergent approach to access extensively functionalized homoallylic sec,tert-vicinal diols frameworks.
View Article and Find Full Text PDFBiocatalytic enantioselective C(sp)-H fluorination enabled by directed evolution of non-haem iron enzymes.
Nat Synth
August 2024
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.
Due to the scarcity of C-F bond forming enzymatic activities in nature and the contrasting ubiquity of organofluorine moieties in bioactive compounds, developing new biocatalytic fluorination reactions represents a preeminent challenge in enzymology, biocatalysis, and synthetic biology. Additionally, catalytic asymmetric C(sp)-H fluorination remains a challenging problem facing synthetic chemists. Although many nonheme Fe halogenases have been discovered to promote C(sp)-H halogenation reactions, to date, efforts to convert these Fe halogenases to fluorinases have remained unsuccessful.
View Article and Find Full Text PDFThe selective amination of aromatic C-H bonds is a powerful strategy to access aryl amines, functionalities found in many pharmaceuticals and agrochemicals. Despite advances in the field, a platform for the direct, selective C-H amination of electronically diverse (hetero)arenes, particularly electron-deficient (hetero)arenes, remains an unaddressed fundamental challenge. In addition, many (hetero)arenes present difficulty in common selective pre-functionalization reactions, such as halogenation, or metal-catalyzed borylation and silylation.
View Article and Find Full Text PDF5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds.
Molecules
January 2025
Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, China.
A Cu-promoted highly chemoselective dimerization of 5-aminopyrazoles to produce pyrazole-fused pyridazines and pyrazines is reported. The protocol generates switchable products via the direct coupling of C-H/N-H, C-H/C-H and N-H/N-H bonds, with the merits of broad substrate scope and high functional group compatibility. Gram-scale experiments demonstrated the potential applications of this reaction.
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