Rhodium(iii)-catalyzed C–H allylation of electron-deficient alkenes with allyl acetates

2015 ◽  
Vol 51 (2) ◽  
pp. 342-345 ◽  
Author(s):  
Chao Feng ◽  
Daming Feng ◽  
Teck-Peng Loh
Keyword(s):  
Functional Group ◽  
Synthetic Pathway ◽  
Reaction Efficiency ◽  
High Reaction ◽  
Directing Group ◽  
Weakly Coordinating

Rhodium-catalyzed C–H allylation of acrylamide derivatives with various allyl acetates was reported. The use of weakly coordinating directing group resulted in high reaction efficiency and excellent γ-selectivity. This reaction displays broad functional group tolerance, which opens a new synthetic pathway for the access of functionalized 1,4-diene skeletons.

scholarly journals Rh(III)-Catalyzed C–H Bond Activation for the Construction of Heterocycles with sp3-Carbon Centers

Catalysts ◽  
2019 ◽  
Vol 9 (10) ◽  
pp. 823 ◽  
Author(s):  
Run Wang ◽  
Xiong Xie ◽  
Hong Liu ◽  
Yu Zhou
Keyword(s):  
Natural Products ◽  
Functional Group ◽  
Bond Activation ◽  
Short Review ◽  
Biological Molecules ◽  
Reaction Conditions ◽  
Reaction Efficiency ◽  
Carbon Centers ◽  
High Reaction ◽  
Privileged Structures

Rh(III)-catalyzed C–H activation features mild reaction conditions, good functional group tolerance, high reaction efficiency, and regioselectivity. Recently, it has attracted tremendous attention and has been employed to synthesize various heterocycles, such as indoles, isoquinolines, isoquinolones, pyrroles, pyridines, and polyheterocycles, which are important privileged structures in biological molecules, natural products, and agrochemicals. In this short review, we attempt to present an overview of recent advances in Rh(III)-mediated C–H bond activation to generate diverse heterocyclic scaffolds with sp3 carbon centers.

Electrophilic Amination with Anthranils through Thioamide-Assisted Cobalt(III)-Catalyzed C(sp3)–H Activation

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3881-3890
Author(s):  
Jie Li ◽  
Lei Liu ◽  
Zhao Zhang ◽  
Yucheng Wang ◽  
Yan Zhang
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Atom Economy ◽  
Electrophilic Amination ◽  
Amino Aldehydes ◽  
Mild Conditions ◽  
Weakly Coordinating

Cobalt(III)-catalyzed electrophilic amination of inert C(sp3)–H bonds of weakly coordinating thioamides with readily accessible anthranil derivatives was accomplished under mild conditions, with good functional group tolerance, thus providing various amino aldehydes and amino ketones. Moreover, our protocol with the versatile [Cp*Co(MeCN)3][SbF6]2 features excellent atom-economy and oxidant-free conditions, and allows facile late-stage functionalization.

scholarly journals Thiocarbonyl-enabled ferrocene C–H nitrogenation by cobalt(III) catalysis: thermal and mechanochemical

2018 ◽  
Vol 14 ◽  
pp. 1546-1553 ◽  
Author(s):  
Santhivardhana Reddy Yetra ◽  
Zhigao Shen ◽  
Hui Wang ◽  
Lutz Ackermann
Keyword(s):  
Functional Group ◽  
Strong Support ◽  
Mechanistic Studies ◽  
Weakly Coordinating

Versatile C–H amidations of synthetically useful ferrocenes were accomplished by weakly-coordinating thiocarbonyl-assisted cobalt catalysis. Thus, carboxylates enabled ferrocene C–H nitrogenations with dioxazolones, featuring ample substrate scope and robust functional group tolerance. Mechanistic studies provided strong support for a facile organometallic C–H activation manifold.

A high performance catalyst for methane conversion to methanol: graphene supported single atom Co

2018 ◽  
Vol 54 (18) ◽  
pp. 2284-2287 ◽  
Author(s):  
Jinyun Yuan ◽  
Wenhua Zhang ◽  
Xingxing Li ◽  
Jinlong Yang
Keyword(s):  
Methane Conversion ◽  
High Performance ◽  
Single Atom ◽  
Reaction Efficiency ◽  
High Reaction

The high reaction efficiency of methane conversion to methanol was predicted over a single atom Co-embedded graphene catalyst.

Cobalt Catalyzed Hydroarylation of Michael Acceptors with Indolines Directed by a Weakly Coordinating Functional Group

2019 ◽  
Vol 21 (11) ◽  
pp. 4049-4053 ◽  
Author(s):  
Shyam Kumar Banjare ◽  
Rajesh Chebolu ◽  
P. C. Ravikumar
Keyword(s):  
Functional Group ◽  
Michael Acceptors ◽  
Weakly Coordinating

Remote meta C–H bond functionalization of 2-phenethylsulphonic acid and 3-phenylpropanoic acid derivatives

2016 ◽  
Vol 52 (96) ◽  
pp. 13916-13919 ◽  
Author(s):  
Atanu Modak ◽  
Anirban Mondal ◽  
Rahul Watile ◽  
Semanti Mukherjee ◽  
Debabrata Maiti
Keyword(s):  
Bond Activation ◽  
Acid Moiety ◽  
Bond Functionalization ◽  
Directing Group ◽  
Weakly Coordinating

This discovery illustrates selective meta C–H bond activation from multiple non-equivalent C–H bonds present in medicinally relevant arylethanesulfonic acid and the 2-arylpropanoic acid moiety using weakly coordinating nitrile as a directing group.

Growing a hydrophilic nanoporous shell on a hydrophobic catalyst interface for aqueous reactions with high reaction efficiency and in situ catalyst recycling

2017 ◽  
Vol 5 (31) ◽  
pp. 16162-16170 ◽  
Author(s):  
Yajuan Hao ◽  
Xuan Jiao ◽  
Houbing Zou ◽  
Hengquan Yang ◽  
Jian Liu
Keyword(s):  
Catalytic Efficiency ◽  
Catalyst Recycling ◽  
Reaction Efficiency ◽  
High Reaction ◽  
Hydrophobic Catalyst ◽  
Aqueous Reactions

We developed a strategy to construct a catalyst with a hydrophobic catalytic interface covered by a hydrophilic, nanoporous shell, which displays high catalytic efficiency and recyclability in aqueous reactions.

scholarly journals Merging Directed C−H Activations with High-Throughput Experimentation: Development of Predictable Iridium-Catalyzed C−H Aminations Applicable to Late-Stage Functionalization

2021 ◽  
Author(s):  
Erik Weis ◽  
Maria Johansson ◽  
Pernilla Korsgren ◽  
Belén Martín-Matute ◽  
Magnus J Johansson
Keyword(s):  
Drug Discovery ◽  
High Throughput ◽  
Late Stage ◽  
Functional Group ◽  
Chemical Space ◽  
Material Consumption ◽  
Modern Drug ◽  
High Throughput Experimentation ◽  
Directing Group ◽  
Group Chemical

Herein, we report an iridium-catalyzed directed C−H amination methodology developed using a high-throughput experimentation (HTE)-based strategy, applicable for the needs of automated modern drug discovery. The informer library approach for investigating accessible directing group chemical space for the reaction, in combination with functional group tolerance screening and substrate scope investigations, allowed for the generation of an empirical predictive model to guide future users. Applicability to late-stage functionalization of complex drugs and natural products, in combination with multiple deprotection protocols leading to the desirable aniline matched pairs, serve to demonstrate the utility of the method for drug discovery. Finally reaction miniaturization to a nano molar range highlights the opportunities for more sustainable screening with decreased material consumption.

scholarly journals Unified and practical access to ɤ-alkynylated carbonyl derivatives via streamlined assembly at room temperature

2019 ◽  
Vol 2 (1) ◽  
Author(s):  
Xu-Lu Lv ◽  
Wei Shu
Keyword(s):  
Carbonyl Group ◽  
Room Temperature ◽  
Functional Group ◽  
Spontaneous Formation ◽  
Carbonyl Derivatives ◽  
Unified Protocol ◽  
Straightforward Method ◽  
Directing Group

Abstract The development of a unified and straightforward method for the synthesis of ɤ-alkynylated ketones, esters, and amides is an unmet challenge. Here we report a general and practical protocol to access ɤ-alkynylated esters, ketones, and amides with diverse substitution patterns enabled by dual-catalyzed spontaneous formation of Csp3–sp3 and Csp3–sp bond from alkenes at room temperature. This directing-group-free strategy is operationally simple, and allows for the straightforward introduction of an alkynyl group onto ɤ-position of carbonyl group along with the streamlined skeleton assembly, providing a unified protocol to synthesize various ɤ-alkynylated esters, acids, amides, ketones, and aldehydes, from readily available starting materials with excellent functional group compatibility.

scholarly journals Investigations into the ligand steric and electronic effects of Ru-catalyzed C–H bond arylation directed by 8-aminoquinoline as a bidentate-directing group

2020 ◽  
Vol 44 (11-12) ◽  
pp. 705-709
Author(s):  
Hamad H. Al Mamari ◽  
Yousuf Al Lawati
Keyword(s):  
Electronic Properties ◽  
Cone Angle ◽  
Phosphine Ligands ◽  
Steric Effects ◽  
Reaction Yield ◽  
Electronic Effects ◽  
Reaction Efficiency ◽  
Alkyl Amines ◽  
Bidentate Phosphine ◽  
Directing Group

In this study, we report an investigation into the steric (cone angle, θ) and electronic properties of ligands in Ru-catalyzed C–H arylation of aromatic benzamides bearing 8-aminoquinoline as an N,N’-bidentate-directing group. The study employs [RuCl2( p-cymene)]2 as a precatalyst, and a ligand, under study, as a cocatalyst. Various electronically and sterically different monodentate and bidentate phosphine ligands were examined. Other ligands such as phosphites and amines were also tested. The study reveals that while bidentate phosphines, phosphites, and aryl and alkyl amines were found to be ineffective, monodentate triarylphosphines represented by triphenylphosphine were found to be the most effective ligands in the Ru-catalyzed C–H arylation under the conditions specified. In addition, the study reveals that there is a correlation between the steric effects, cone angle (θ) and the reaction efficiency. Thus, for symmetrical phosphine ligands, as the cone angle increases, the yield of the CH arylation product gradually decreased. Moreover, the electronic properties of triarylphosphine ligands influenced the reaction as demonstrated by the decreased ability of electron-poor ligands to promote the reaction. The study also reveals a correlation between the electronic parameter, υCO, of the triarylphosphine ligand and the reaction efficiency. As the carbonyl stretching frequency increases, the reaction yield gradually decreased.

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