Ruthenium-Catalyzed Intramolecular Cycloaddition of Cyclopropenynes and Cyclopropendiynes DOI
Martin Oestreich, Hendrik F. T. Klare,

Emilio Acuña Bolomey

et al.

Synfacts, Journal Year: 2023, Volume and Issue: 19(10), P. 1007 - 1007

Published: Sept. 14, 2023

Key words cycloheptatrienes - cyclopentadienes cyclopropenynes cyclopropendiynes ruthenium catalysis

Language: Английский

Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters DOI Creative Commons
Ziying Wang, Shoujun Wang,

Nan‐Nan Dai

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 24, 2025

C–C bond cleavage and recombination provide an efficient strategy for the modification reconstruction of molecule structures. Herein, we present a method achieving amidation aryl C(sp2)–H through triple with involvement nitrous acid esters. This marks instance precise controlled stepwise bond, offering fresh perspective such bonds. Nitrous ester serves as both radical source hydrogen atom transfer (HAT) reagent to functionalize utilize two carbon atoms bond. The alkoxy captures from or N-hydroxyl induce 1,3-oxygen migration, which is crucial subsequent molecular authors report achieve bonds by participation

Language: Английский

Citations

3
Rhodium-Catalyzed [5 + 1 + 2] Reaction of Yne-Vinylcyclopropenes and CO: The Application of Vinylcyclopropenes for Higher-Order Cycloaddition DOI
Zhiqiang Huang, Zhi‐Xiang Yu

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

Published: April 30, 2025

Transition metal-catalyzed higher-order cycloadditions involving vinylcyclopropenes (VCPEs) have not been realized to synthesize challenging medium-sized rings, partially due their poor stability and many competing side reactions. We report here a Rh-catalyzed [5 + 1 2] reaction of yne-VCPEs CO for the synthesis eight-membered carbocycles with trienone moiety, which so far can be accessed by only limited The key this cycloaddition is that once C-C cleavage VCPE (C5 synthon) form six-membered metallacycle initiated, (C1 insertion happens before alkyne (C2 insertion, attributing special reactivity sp2 carbon in vinylcyclopropene. Quantum chemical calculations applied support pathway. present has broad scope, C2 synthon also extended alkenes allene. Of same importance, catalyzed either [Rh(CO)2Cl]2 or cheaper complex, RhCl3·nH2O.

Language: Английский

Citations

0
Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels–Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles DOI
Andrés Felipe León Rojas,

Ying Yan Chong,

Sara H. Kyne

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3037 - 3042

Published: April 1, 2024

A synthetic method for the enantioselective and regiodivergent synthesis of hexahydro-2H-2,4a-methanonaphthalen-4-yl octahydro-2,4-methanoazulen-1-yl esters that relies on gold(I)- chiral Brønsted acid-catalyzed cycloisomerization/Diels–Alder (CDA) reaction (E)-1,10-dien-4-yn-3-yl acetates is described.

Language: Английский

Citations

2
Cobalt-Catalyzed (3 + 2) Cycloaddition of Cyclopropene-Tethered Alkynes: Versatile Access to Bicyclic Cyclopentadienyl Systems and Their CpM Complexes DOI Creative Commons
Carlos Lázaro‐Milla, Eduardo da Concepción, Israel Fernández

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11574 - 11583

Published: July 20, 2024

Low-valent cobalt complexes can promote intramolecular (3 + 2) cycloadditions of alkyne-tethered cyclopropenes to provide bicyclic systems containing highly substituted cyclopentadienyl moieties with electronically diverse functional groups. The adducts be easily transformed into new types CpRh(III) and CpIr(III) complexes, which show catalytic activity in several relevant transformations. Preliminary computational (DFT) experimental studies information on the mechanistic peculiarities cobalt-catalyzed process allow us rationalize its advantages over homologous rhodium-promoted reaction.

Language: Английский

Citations

2
Synthesis of Multisubstituted Cyclopentadiene Derivatives from 3,3-Disubstituted Cyclopropenes and Internal Alkynes Catalyzed by Low-Valent Niobium Complexes DOI
Takuya Akiyama, Tetsuro Kusamoto, Kazushi Mashima

et al.

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

Published: Nov. 22, 2024

A low-valent niobium species generated from NbCl

Language: Английский

Citations

2
Engaging Isatins and Amino Acids in Multicomponent One-Pot 1,3-Dipolar Cycloaddition Reactions—Easy Access to Structural Diversity DOI Creative Commons
Hua Zhao, Yufen Zhao

Molecules, Journal Year: 2023, Volume and Issue: 28(18), P. 6488 - 6488

Published: Sept. 7, 2023

Multicomponent reactions (MCRs) have undoubtedly emerged as the most indispensable tool for organic chemists worldwide, finding extensive utility in synthesis of intricate natural products, heterocyclic molecules with significant bioactivity, and pharmaceutical agents. The multicomponent one-pot 1,3-dipolar cycloaddition reactions, which were initially conceptualized by Rolf Huisgen 1960, find application contemporary chemistry. In terms green synthesis, is highly favored owing to its numerous advantages, including high step- atom-economies, remarkable product diversity, well excellent efficiency diastereoselectivity. Among pieces research, fascinating reaction involves utilization azomethine ylides generated from isatins amino acids that can be captured various dipolarophiles. This approach offers a efficient convenient method constructing spiro-pyrrolidine oxindole scaffolds, are crucial building blocks biologically active molecules. Consequently, this review delves deeper into dipolarophiles utilized over past six years.

Language: Английский

Citations

6
Cobalt/Photoredox Cooperative Catalysis‐Enabled Cycloaddition Reactions of 1,6‐Diynes and Related Compounds DOI Creative Commons
Takeshi Yasui, Yoshihiko Yamamoto

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

Published: April 8, 2024

Abstract Cobalt catalysts have recently gained considerable attention as alternatives to based on precious transition metals such Rh and Ir. Recently, Co/photoredox cooperative catalysis has emerged a powerful tool that enables versatile transformations, including cycloaddition reactions of unsaturated compounds. In particular, 1,6‐diyne derivatives are fascinating substrates for these because the corresponding exocyclic 1,3‐diene products can be further transformed into sp 3 ‐rich carbocycles heterocycles via functionalization diene moiety. The dual catalytic system facilitate not only activation π‐bond only, alkyne cyclotrimerization, but also involving σ‐bond activation. This Concept highlights recent advances in cooperative‐catalysis‐enabled reactions, focusing substrates, which difficult perform when well‐defined cationic Co I is employed.

Language: Английский

Citations

1
Transition-metal-free isofunctional reaction of α,β-unsaturated ketones/nitriles DOI

Runyou Ye,

Jialin Ming,

Qinyue Tao

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 29, 2024

Language: Английский

Citations

1
Ruthenium-Catalyzed Intramolecular Cycloaddition of Cyclopropenynes and Cyclopropendiynes DOI
Martin Oestreich, Hendrik F. T. Klare,

Emilio Acuña Bolomey

et al.

Synfacts, Journal Year: 2023, Volume and Issue: 19(10), P. 1007 - 1007

Published: Sept. 14, 2023

Key words cycloheptatrienes - cyclopentadienes cyclopropenynes cyclopropendiynes ruthenium catalysis

Language: Английский

Citations

0