Photoinduced, Copper-Catalyzed Enantioconvergent Synthesis of β-Aminoalcohol Derivatives

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Март 24, 2025

In view of the frequent occurrence carbon-nitrogen bonds in organic compounds, development powerful new methods for construction such is expected to greatly impact many fields that utilize molecules. While substitution an alkyl electrophile by a nitrogen nucleophile seemingly straightforward approach generating bond, practice classical pathways have very substantial limitations case unactivated secondary and tertiary electrophiles. Recent reports transition metals can catalyze certain reactions electrophiles are therefore considerable significance; however, virtually no been developed wherein absolute stereochemistry controlled together with bond formation. Herein, we address this dual challenge reactivity enantioselectivity, describing photoinduced, copper-catalyzed enantioconvergent synthesis β-aminoalcohol derivatives via coupling anilines racemic, β-haloethers. We apply method catalytic asymmetric metolachlor, report array mechanistic studies consistent reaction pathway propose.

Язык: Английский

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Recent Advances in Palladium-Catalyzed Enantioselective Cyclization for the Construction of Atropisomers

Catalysts, Год журнала: 2025, Номер 15(4), С. 320 - 320

Опубликована: Март 27, 2025

Axially chiral structures have become increasingly common in modern materials and pharmaceuticals, especially as ligands organocatalysts, highlighting their growing significance. In the field of pharmaceutical research, there are several notable examples worth highlighting, such antibiotics vancomycin, Knipholone, Mastigophorene A. Over past decade, availability axially compounds has significantly improved through advancements existing strategies introduction catalytic atroposelective synthesis concepts. These synthetic not only broaden scope chemical reactions, but also facilitate construction frameworks with high application value. Currently, various methods available for achieving stereoselective under catalyst control, including desymmetrization, (dynamic) kinetic resolution, cross-coupling de novo ring-forming synthesis. This paper focuses on recent advances constructing atropisomers palladium-catalyzed asymmetric cyclization strategies.

Язык: Английский

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Copper-Catalyzed Reductive Hydroamination of Inactive Diarylacetylenes with Nitroarenes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 17, 2025

Reductive hydroamination of stable and readily available nitroarenes with unsaturated hydrocarbons represents practical access to amines. Herein, we report a simple Cu-catalyzed amine synthesis via the reductive inactive diarylacetylenes. A series diarylacetylenes are successfully transformed into secondary amines under mild conditions good functional group tolerance.

Язык: Английский

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Rhodium(III)-Catalyzed Redox-Neutral [4 + 2] Annulation of 3,5-Diaryloxadiazoles with Alkynes: A Dual C–H Activation Strategy for Constructing C–N Atropisomers

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 22, 2025

A rhodium(III)-catalyzed dual-ring formation via cascade C-H activation/[4 + 2] annulation of 3,5-diaryoxadiazoles with alkynes was developed. This strategy has been demonstrated a variety 3,5-diaryloxadiazoles and alkynes, it successfully scaled up to gram-scale synthesis, highlighting its potential significance in the direct construction C-N atropisomers. Furthermore, cleavage N-O bond is essential for bicyclic structure absence an external oxidant. Mechanistic studies revealed that at 3-phenyl group oxadiazole likely rate-determining step this reaction.

Язык: Английский

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Copper-Catalyzed Asymmetric Nucleophilic Opening of 1,1,2,2-Tetrasubstituted Donor–Acceptor Cyclopropanes for the Synthesis of α-Tertiary Amines

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Дек. 26, 2024

Catalytic asymmetric transformation of donor–acceptor cyclopropanes (DACs) has been proven to be a highly valuable and robust strategy construct diverse types enantioenriched molecules. However, the use 1,1,2,2-tetrasubstituted DACs form products bearing quaternary stereocenters remains long-term unsolved challenge. Here, we report copper-catalyzed aminative ring opening tetrasubstituted alkynyl that delivers myriad α-tertiary amines with high levels enantioselectivities. The alkyne, amine, ester moieties within enable further applications, including synthesis bioactive Mechanistic studies indicate zwitterionic intermediate copper-acetylide unit plays key role in process, which represents new mode for achieving catalytic DACs.

Язык: Английский

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Synthesis of Quinoline–Indole Hybrids through Cu(II)-Catalyzed Amination and Annulation between N-Oxides and o-Alkynylanilines

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 16, 2024

The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline N-oxides with o-alkynylanilines in the presence a combination copper(II) catalyst and bidentate 2,2′-bipyridine ligand is described. utility this method was demonstrated through site-selective functionalization synthesized products. A plausible reaction pathway for amination followed annulative indole formation elucidated series mechanistic investigations.

Язык: Английский

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Photocatalyzed amination of benzylic C(sp3)−H bonds via C−N coupling: Green synthesis and NMR analysis of N-benzylanilines

Journal of Molecular Structure, Год журнала: 2024, Номер 1322, С. 140699 - 140699

Опубликована: Ноя. 9, 2024

Язык: Английский

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Heterogeneous electrocatalytic synthesis of nitrogenous organic compounds using inorganic nitrogen sources

Nano Materials Science, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 1, 2024

Язык: Английский

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Enantioselective Synthesis of the Aggregation Pheromone of Odontothrips loti (Haliday) and Its Stereoisomers

ChemistrySelect, Год журнала: 2024, Номер 9(46)

Опубликована: Дек. 1, 2024

Abstract Odontothrips loti (Haliday) is a thrip pest of leguminous plants. The aggregation pheromone this and its stereoisomers have been synthesized. central strategy involved enantioselective cross‐coupling racemic benzyl 2‐bromopropanoate with alkenyl Grignard, Evans’ chiral auxiliaries Yamaguchi esterification 2‐methylbutanoic acid lavandulol.

Язык: Английский

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Advancements in Chan-Lam cross-coupling reactions utilizing copper and nickel salts, Cu/Ni-incorporated polymers, and nanocomposites

Inorganic Chemistry Communications, Год журнала: 2024, Номер unknown, С. 113799 - 113799

Опубликована: Дек. 1, 2024

Язык: Английский

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