4.7 Article

An efficient ruthenium(IV) catalyst for the selective hydration of nitriles to amides in water under mild conditions

期刊

CHEMICAL COMMUNICATIONS
卷 50, 期 68, 页码 9661-9664

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4cc04058a

关键词

-

资金

  1. MINECO of Spain [CTQ2010-14796/BQU]
  2. Spanish Government
  3. ESF

向作者/读者索取更多资源

A Ru(IV) catalyst able to promote the selective hydration of nitrites to amides in water, at low metal loadings and under mild conditions, is presented.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.7
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Review Chemistry, Physical

Metal-Catalyzed Synthesis and Transformations of β-Haloenol Esters

Victorio Cadierno

CATALYSTS (2020)

Review Chemistry, Organic

Recent Advances in the Transition Metal-Catalyzed Addition of Carboxylic Acids to Alkynes

Vittorio Cadierno

Summary: Recent developments in the metal-catalyzed hydrofunctionalization of alkynes with carboxylic acids are comprehensively reviewed in this study, with a focus on both inter- and intramolecular processes and their implications in the synthesis of natural products and biologically active molecules. This review also highlights the use of cascade processes for the assembly of complex heterocyclic compounds.

CURRENT ORGANIC CHEMISTRY (2021)

Editorial Material Chemistry, Physical

Recent Advances in Organometallic Chemistry and Catalysis

Victorio Cadierno

CATALYSTS (2021)

Article Chemistry, Multidisciplinary

Critical Assessment of the Reducing Ability of Breslow-type Derivatives and Implications for Carbene-Catalyzed Radical Reactions**

Ludivine Delfau, Samantha Nichilo, Florian Molton, Julie Broggi, Eder Tomas-Mendivil, David Martin

Summary: This study reported the synthesis of acyl azolium salts from various types of carbenes and the generation of their corresponding radicals and enolates, revealing the role of additives in the redox behavior of these compounds and correcting misconceptions about radical transformations of aldehyde derivatives. The reducing ability of enolates derived from certain carbenes was found to be underestimated, and catalytic intermediates were shown to transfer electrons efficiently at room temperature. Enol derivatives of certain carbenes were identified as powerful reducing agents.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

Catalytic Hydrofunctionalization Reactions of 1,3-Diynes

Victorio Cadierno

Summary: Metal-catalyzed hydrofunctionalization reactions of alkynes, especially conjugated 1,3-diynes, have been extensively studied. These reactions provide a straightforward and efficient route to functionalized olefins and various heterocyclic and carbocyclic compounds. However, the regio- and stereocontrol issues associated with conjugated 1,3-diynes make the hydrofunctionalization reactions challenging.

CATALYSTS (2022)

Article Chemistry, Organic

One-Pot Synthesis of Push-Pull Butadienes from 1,3-Diethyl-2-thiobarbituric Acid and Propargylic Alcohols

Javier Francos, Victorio Cadierno

Summary: This study presents a new synthetic procedure for obtaining two previously reported donor-acceptor butadiene dyes. The reactions proceed in water under MW irradiation and the target products were characterized using various analysis methods.

MOLBANK (2022)

Article Chemistry, Multidisciplinary

An air-stable radical with a redox-chameleonic amide

Jesse L. Peltier, Melinda R. Serrato, Valentin Thery, Jacques Pecaut, Eder Tomas-Mendivil, Guy Bertrand, Rodolphe Jazzar, David Martin

Summary: An air-stable (amino)(amido)radical was prepared by the reaction of a cyclic (alkyl)(amino)carbene with carbazoyl chloride, followed by one-electron reduction. The neighboring radical center was found to weaken the amide bond, enabling the amino group to serve as a strong acceptor under steric constraint and enhancing the stabilizing captodative effect.

CHEMICAL COMMUNICATIONS (2023)

Article Chemistry, Organic

Bending Enamine Patterns of Stabilized Pentalenes into ?Polymethine Ylides?

Valentin Thery, Cyriac Barra, Alexandra Simeoni, Jacques Pecaut, Eder Tomas-Mendivil, David Martin

Summary: This paper reports the synthesis and structural study of 2-substituted 1,3-bis(dimethylamino)pentalenes. The substituents donate two electrons, shifting the aromatic pattern to more suitable polarized structures. Depending on the steric trade-off, either planar cyclopentadienyl vinamidiniums or distorted structures featuring a pyramidalized ylidic carbon adjancent to a stabilized pi-conjugated iminium can be obtained. This study provides insights into unconventional distorted conformations of organic molecules.

ORGANIC LETTERS (2023)

Article Chemistry, Multidisciplinary

Beyond the Limits of Atropochirality: Design of Highly Conformationally Restrained Biaryls with Bridgehead Phosphine Oxide

Lucas Mele, Rachida Babouri, Jean-Luc Pirat, Eder Tomas-Mendivil, David Martin, Tahar Ayad, David Virieux

Summary: In the past 30 years, researchers have shown great interest in synthesizing atropochiral biaryls with steric congestion on the ortho-substituted arenes. This study presents an efficient approach to produce a new class of 2,2' disubstituted biaryls bridgehead phosphine oxides with exceptional conformational stability. The researchers found that by replacing only one hydrogen atom at the ortho position with a fluorine atom, the rotation of the biaryl backbone can be restricted at temperatures below 80°C, significantly extending the limits of atropostability. Additionally, their investigations revealed unique insights into the isomerization mechanism of these molecules.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

Review Chemistry, Physical

Gold Complexes with Hydrophilic N-Heterocyclic Carbene Ligands and Their Contribution to Aqueous-Phase Catalysis

Pascale Crochet, Victorio Cadierno

Summary: N-Heterocyclic carbenes (NHCs) are widely used ligands in organometallic chemistry and catalysis due to their stability and flexibility. By functionalizing NHCs with hydrophilic groups, they can be used in aqueous catalysis, which is a hot topic in Green Chemistry. This review summarizes the research on hydrophilic NHC-gold catalysts and the catalytic applications of water-soluble gold nanoparticles stabilized by hydrophilic NHCs.

CATALYSTS (2023)

Article Chemistry, Multidisciplinary

On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis

Ludivine Delfau, Nadhrata Assani, Samantha Nichilo, Jacques Pecaut, Christian Philouze, Julie Broggi, David Martin, Eder Tomas-Mendivil

Summary: We isolated and studied dimers derived from popular thiazol-2-ylidene organocatalysts. The model compound with 2,6-di(isopropyl)phenyl (Dipp) N-substituents was found to be a stronger reducing agent compared to previously studied bis(thiazol-2-ylidenes). Furthermore, the significant potential difference between the first and second oxidation of the dimer allows for the isolation of an air-persistent radical cation, which efficiently promotes the radical transformation of alpha-bromoamides into oxindoles.

ACS ORGANIC & INORGANIC AU (2023)

Article Chemistry, Organic

Bending Enamine Patterns of Stabilized Pentalenes into Polymethine Ylides

Valentin Thery, Cyriac Barra, Alexandra Simeoni, Jacques Pecaut, Eder Tomas-Mendivil, David Martin

Summary: We report the synthesis and structural study of 2-substituted 1,3-bis(dimethylamino)pentalenes, which exhibit shifted polarized structures due to the electron-donating substituents. Depending on the steric effects, the compounds can adopt planar cyclopentadienyl vinamidiniums or distorted structures mimicking key Breslow intermediates in thiamine-dependent enzymes. This study highlights the use of avoiding anti-aromaticity in accessing unconventional distorted conformations of organic molecules.

ORGANIC LETTERS (2023)

Article Chemistry, Multidisciplinary

The curious case of a sterically crowded Stenhouse salt

Valentin Thery, Florian Molton, Selim Sirach, Neven Tillet, Jacques Pecaut, Eder Tomas-Mendivil, David Martin

Summary: In this study, we report a peculiar Stenhouse salt that does not undergo cyclopentenones formation upon basification due to the steric hindrance of its bulky stable carbene patterns. This unique feature allowed us to observe and characterize the transient open-chain neutral derivative, which was isolated in its cyclized form. The cyclized form exhibits an unusually long reactive C-O bond (150 pm) and demonstrates rich electrochemistry, including oxidation into an air-persistent radical cation.

CHEMICAL SCIENCE (2022)

Review Chemistry, Inorganic & Nuclear

Arene-Osmium(II) Complexes in Homogeneous Catalysis

Pascale Crochet, Victorio Cadierno

Summary: This review article focuses on the catalytic applications of arene-osmium(II) complexes, discussing transfer hydrogenation, hydrogenation, oxidation, and nitrile hydration reactions, as well as different C-C bond forming processes comprehensively, showing that they can achieve comparable or superior effectiveness in some instances compared to their ruthenium analogues.

INORGANICS (2021)

Article Chemistry, Organic

N-[(1R)-1-(4-Chlorophenyl)ethyl]-Cyanamide

Rebeca Gonzalez-Fernandez, Pascale Crochet, Victorio Cadierno

Summary: The title compound was synthesized by electrophilic cyanation of commercially available (R)-4-chloro-alpha-methylbenzylamine, yielding a yellow oil in 84% yield. It was characterized using various methods such as H-1 and C-13{H-1] NMR, IR, HRMS, and specific rotation measurements.

MOLBANK (2021)

Review Chemistry, Multidisciplinary

Trap suppression in ordered organic photovoltaic heterojunctions

Dan He, Yawen Li, Fuwen Zhao, Yuze Lin

Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.

CHEMICAL COMMUNICATIONS (2024)

Review Chemistry, Multidisciplinary

Controversial mechanism of simultaneous photocatalysis and Fenton-based processes: additional effect or synergy?

Olivier Monfort, Arshitha Madhusudhan, Martin Motola

Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Polymerization of monomer aggregates for tailoring and patterning water wettability

Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna

Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Pd/Brønsted acid catalysed intramolecular N-allylation of indoles and pyrroles with alkynes for the synthesis of N-fused heterocycles

Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi

Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Rh(III)-catalyzed selective mono- and dual-functionalization/cyclization of 1-aryl-5-aminopyrazoles with iodonium ylides

Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang

Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Modified minimal-size fragments of heparan sulfate as inhibitors of endosulfatase-2 (Sulf-2)

Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell

Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Reductive cyclodimerization of chalcones: exploring the self-adaptability of galvanostatic electrosynthesis

Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini

Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Rh(III)-catalyzed oxidative [4+2] annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols

Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar

Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

PbTeB4O9: a lead tellurium borate with unprecedented fundamental building block [B4O10] and large birefringence

Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan

Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Wafer-scale synthesis of two-dimensional ultrathin films

Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal

Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Precise design of copolymer-conjugated nanocatalysts for active electron transfer

Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi

Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.

CHEMICAL COMMUNICATIONS (2024)