A catalytic system based on π–π stacking interactions between a pyrene substituted gold NHC catalyst and amphiphilic polymers for alkyne hydration reactions DOI
Bengi Özgün Öztürk,

Hilal Acar,

Ayşegül Balcı

et al.

Dalton Transactions, Journal Year: 2023, Volume and Issue: 52(38), P. 13587 - 13593

Published: Jan. 1, 2023

Pyrene-substituted amphiphilic polymers (P1) were used to stabilize the pyrene-substituted gold complex (Au-1) within hydrophobic compartment of micellar structures in a methanol/water mixture through non-covalent π–π stacking interactions.

Language: Английский

Asymmetric gold catalysis enabled by specially designed ligands DOI
Amol B. Gade,

Urvashi Urvashi,

Nitin T. Patil

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1858 - 1895

Published: Jan. 1, 2024

This review is planned to provide a comprehensive overview of the progress made in design and development chiral ligands for asymmetric gold catalysis.

Language: Английский

Citations

13

Transition-metal-, oxidant- and additive-free multi-component synthesis of alkyl heteroaryl BCPs enabled by visible-light-induced phosphine-catalyzed halogen-atom transfer DOI
Jun Xu,

Yu Hong,

Ruiyuan Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This study describes a pioneering visible-light-induced phosphine-catalyzed halogen-atom transfer (XAT) strategy that heralds new era in the difunctionalization of [1.1.1]propellane.

Language: Английский

Citations

12

Enantioselective merged gold/organocatalysis DOI
Chayanika Pegu, Bidisha Paroi, Nitin T. Patil

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(27), P. 3607 - 3623

Published: Jan. 1, 2024

This highlight demonstrates the state of art in field enantioselective merged gold/organocatalysis by leveraging unique reactivity each catalyst.

Language: Английский

Citations

8

Trinuclear Gold‐Catalyzed 1,2‐Difunctionalization of Alkenes DOI

Qing‐Yun Fang,

Jie Han,

Mingzhe Qin

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(34)

Published: May 12, 2023

Activated alkyl halides have been extensively explored to generate radicals with Ru- and Ir- photocatalysts for 1,2-difunctionalization of alkenes, but unactivated bromides remain challenging substrates due their strong reduction potential. Here we report a three-component reaction nucleophiles (e.g., amines indoles) using trinuclear gold catalyst [Au3 (tppm)2 ](OTf)3 . It can achieve the 1,2-aminoalkylation 1,2-alkylarylation readily. This protocol has broad scope excellent functional group compatibility (>100 examples up 96 % yield). also affords robust formal [2+2+1] cyclization strategy concise construction pyrrolidine skeletons under mild conditions. Mechanistic studies support an inner-sphere single electron transfer pathway successful cleavage inert C-Br bonds.

Language: Английский

Citations

13

Overview of Transition Metal Catalyzed Multicomponent Reactions Based on Trapping of Allylic Electrophiles DOI

Kriti Gupta,

Mahesh Singh Harariya,

Arushi Tyagi

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(4)

Published: Jan. 11, 2024

Abstract Multicomponent reactions provide an excellent approach toward quaternary carbon centres utilizing convergent chemical in a highly selective manner under one‐pot conditions. The reactivity of substrates and metal catalysts is carefully controlled, precluding the formation side‐products. In this context, transition catalyzed onium ylides generated via diazo precursors nucleophiles with third component (an electrophile) have garnered significant attention. Using allylic precursor as electrophilic partner provides opportunities to construct all‐carbon centres. Furthermore, presence allyl fragment multicomponent product serves pivotal handle for carrying out subsequent modifications. Several recent studies employed Rh, Pd, dual Rh/Pd catalytic systems involving alkylation that proceed synergistic or relay pathway. Although not significantly successful, few cases, asymmetric induction achieved through chiral phosphoric acids phosphine ligands. Limited substrate catalyst scope underlying mechanistic complexities posed formidable challenges, slowing advancement reactions. This review details using readily available like compounds, carbonates, (R‐OH, R‐NH 2 , etc .) forming complex organic compounds. Our primary objective discuss issues may facilitate progress field.

Language: Английский

Citations

5

Gold-Catalyzed 1,2-Carboxyarylation of Alkenes DOI
Tanmayee Nanda, Avishek Das,

Prafulla Bera

et al.

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

Published: Feb. 24, 2025

Herein, we disclose an unprecedented gold-catalyzed 1,2-carboxyarylation of alkenes through ligand-enabled Au(I)/Au(III) catalysis. Unlike other approaches for the arylative functionalization C-C multiple bonds, attempts to utilize weak nucleophiles such as carboxylate anions were unsuccessful. The key achieving this transformation is use a 1,3-diketone-appended alkene, which undergoes oxyarylation followed by retro-aldol reaction afford product. Detailed mechanistic investigations conducted support proposed mechanism.

Language: Английский

Citations

0

Gold-catalyzed four-component multifunctionalization of alkynes DOI Creative Commons

Shangwen Fang,

Jie Han, Chengjian Zhu

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: June 15, 2023

The alkyne unit is a versatile building block in organic synthesis and the development of selective multifunctionalization alkynes an important object research this field. Herein, we report interesting gold-catalyzed, four-component reaction that achieves oxo-arylfluorination or oxo-arylalkenylation internal aromatic aliphatic alkynes, efficiently breaking carbon-carbon triple bond forming four new chemical bonds. divergence can be controlled by site-directing functional groups alkynes; presence phosphonate favors oxo-arylfluorination, while carboxylate motif benefits oxo-arylalkenylation. This enabled Au(I)/Au(III) redox coupling process using Selectfluor as both oxidant fluorinating reagent. A wide range structurally diverse α,α-disubstituted ketones, tri- tetra-substituted unsaturated ketones have been prepared synthetically valuable yields with excellent chemo-, regio- stereoselectivity. gram-scale preparation late-stage application complex further enhanced their synthetic value.

Language: Английский

Citations

9

Metalated covalent organic frameworks as efficient catalysts for multicomponent tandem reactions DOI

Xuan Kan,

Jian‐Cheng Wang, Yu‐Bin Dong

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(50), P. 6362 - 6374

Published: Jan. 1, 2024

Multicomponent tandem reactions have become indispensable synthetic methods due to their economic advantages and efficient usage in natural products drug synthesis. The emergence of metalated covalent organic frameworks (MCOFs) has opened up new opportunities for the advancement multicomponent reactions. In contrast commonly used homogeneous transition metal catalysts, MCOFs possess regular porosity, high crystallinity, rich chelation sites that facilitate uniform distribution anchoring metals within cavities. Thus, they show extremely activity recently been widely employed as catalysts It is timely conduct a review reactions, order offer guidance assistance synthesis MCOF application This provides comprehensive overview design MCOFs, progress primary challenges encountered during current development with aim contributing promotion field.

Language: Английский

Citations

3

A photoinduced multicomponent intramolecular cyclization/hydroxytrifluoromethylation cascade: facile access to polyfunctionalized 3,4-dihydroquinazolinones DOI
Changjun Zhang,

Yuxin Ding,

Wenkai Huang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(4), P. 2094 - 2101

Published: Jan. 1, 2024

Herein, we report a modular assembly of CF 3 -modified 3,4-dihydroquinazolinones from basic building blocks using one-pot light-driven multicomponent approach.

Language: Английский

Citations

2

New Avenues for the Synthesis of Oxa‐Cycles Using Lewis/Brønsted Acid mediated Carboxygenation and Carboalkoxylation of Alkynes DOI
Santosh K. Nanda, Laxmi Narayan Nanda, Juhi Pal

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(19)

Published: April 16, 2024

Abstract The cascade functionalizations of alkynes have provided many elegant methods for the synthesis useful scaffolds. Amongst these functionalizations, ones comprising C−C and C−O bond formation been utilized extensively due to abundant presence oxygenated motifs in various bio‐active natural as well unnatural products. Transition‐metal catalysis is a mainstay tandem they are very efficient. However, their utilization does typically involve stoichiometric additives like other metal salts and/or Lewis acids/Brønsted acids (LA/BA). Thus, approaches that rely solely on using LA/BA, make vital transformations not only eco‐friendly atom economical but also cost beneficial fast emerging complementary alternatives. present review addresses gap literature by summarizing recent developments LA/BA mediated 1,1/1,2‐carboxygenation carboalkoxylation oxa‐cycles. reaction mechanisms particularly emphasized bring out understanding needed from point future this domain.

Language: Английский

Citations

2