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

Chang-qiu Lin,

Si-ying Ren

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1322, P. 140699 - 140699

Published: Nov. 9, 2024

Language: Английский

Photoinduced, Copper-Catalyzed Enantioconvergent Synthesis of β-Aminoalcohol Derivatives DOI
Arup Mondal, Gregory C. Fu

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 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.

Language: Английский

Citations

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

Shouang Lan,

Qinqin Cui,

Defu Luo

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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.

Language: Английский

Citations

4
Recent Advances in Palladium-Catalyzed Enantioselective Cyclization for the Construction of Atropisomers DOI Open Access
Xilong Wang, Wei Ren, Jingyi Zhang

et al.

Catalysts, Journal Year: 2025, Volume and Issue: 15(4), P. 320 - 320

Published: March 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.

Language: Английский

Citations

0
Copper-Catalyzed Reductive Hydroamination of Inactive Diarylacetylenes with Nitroarenes DOI
Zhiyou Li,

Jie Tang,

Xinyue Ma

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

Citations

0
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 DOI
Siyuan Li, Yong Han, Zhen Yang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

Citations

0
Heterogeneous electrocatalytic synthesis of nitrogenous organic compounds using inorganic nitrogen sources DOI Creative Commons
Chao Wang, Jialu Li, Flemming Besenbacher

et al.

Nano Materials Science, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Language: Английский

Citations

1
Synthesis of Quinoline–Indole Hybrids through Cu(II)-Catalyzed Amination and Annulation between N-Oxides and o-Alkynylanilines DOI
Amitava Rakshit,

Kyeongwon Moon,

Pargat Singh

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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.

Language: Английский

Citations

1
Enantioselective Synthesis of the Aggregation Pheromone of Odontothrips loti (Haliday) and Its Stereoisomers DOI Open Access
Jianan Wang, Xueyang Wang,

Biyu An

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(46)

Published: Dec. 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.

Language: Английский

Citations

0
Advancements in Chan-Lam cross-coupling reactions utilizing copper and nickel salts, Cu/Ni-incorporated polymers, and nanocomposites DOI
Palani Sasikumar‬‬‬‬, Anjoy Majhi

Inorganic Chemistry Communications, Journal Year: 2024, Volume and Issue: unknown, P. 113799 - 113799

Published: Dec. 1, 2024

Language: Английский

Citations

0
Photocatalyzed amination of benzylic C(sp3)−H bonds via C−N coupling: Green synthesis and NMR analysis of N-benzylanilines DOI
Hongbo Tan,

Chang-qiu Lin,

Si-ying Ren

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1322, P. 140699 - 140699

Published: Nov. 9, 2024

Language: Английский

Citations

0