ChemInform Abstract: Chiral Auxiliary-Based C-C Bond Forming Reactions - Still a Fundamental Route to Complex Molecules of High Enantiomeric Purity

ChemInform ◽  
2010 ◽  
Vol 28 (4) ◽  
pp. no-no
Author(s):  
A. I. MEYERS
Keyword(s):  
Enantiomeric Purity ◽  
Chiral Auxiliary ◽  
Complex Molecules ◽  
Bond Forming ◽  
Bond Forming Reactions

scholarly journals Copper-catalysed alkylation of heterocyclic acceptors with organometallic reagents

2020 ◽  
Vol 16 ◽  
pp. 1006-1021
Author(s):  
Yafei Guo ◽  
Syuzanna R Harutyunyan
Keyword(s):  
Natural Products ◽  
Frequent Occurrence ◽  
Bioactive Molecules ◽  
Complex Molecules ◽  
Organometallic Reagents ◽  
Bond Forming ◽  
The Past ◽  
Bond Forming Reactions

Copper-catalysed asymmetric C–C bond-forming reactions using organometallic reagents have developed into a powerful tool for the synthesis of complex molecules with single or multiple stereogenic centres over the past decades. Among the various acceptors employed in such reactions, those with a heterocyclic core are of particular importance because of the frequent occurrence of heterocyclic scaffolds in the structures of chiral natural products and bioactive molecules. Hence, this review focuses on the progress made over the past 20 years for heterocyclic acceptors.

Metal-Free Photoredox-Catalyzed C–H/C–H Coupling of Arenes Enabled by Interrupted Pummerer Activation

2019 ◽  
Author(s):  
Miles Aukland ◽  
Mindaugas Šiaučiulis ◽  
Adam West ◽  
Gregory Perry ◽  
David Procter
Keyword(s):  
Natural Product ◽  
Selective Reduction ◽  
Cross Coupling ◽  
One Pot ◽  
Complex Molecules ◽  
Pummerer Reaction ◽  
Metal Free ◽  
Bond Forming ◽  
Coupling Partner ◽  
Bioactive Natural Product

<p>Aryl–aryl cross-coupling constitutes one of the most widely used procedures for the synthesis of high-value materials, ranging from pharmaceuticals to organic electronics and conducting polymers. The assembly of (hetero)biaryl scaffolds generally requires multiple steps; coupling partners must be functionalized before the key bond-forming event is considered. Thus, the development of selective C–H arylation processes in arenes, that side-step the need for prefunctionalized partners, is crucial for streamlining the construction of these key architectures. Here we report an expedient, one-pot assembly of (hetero)biaryl motifs using photocatalysis and two non-prefunctionalized arene partners. The approach is underpinned by the activation of a C–H bond in an arene coupling partner using the interrupted Pummerer reaction. A unique pairing of the organic photoredox catalyst and the intermediate dibenzothiophenium salts enables highly selective reduction in the presence of sensitive functionalities. The utility of the metal-free, one-pot strategy is exemplified by the synthesis of a bioactive natural product and the modification of complex molecules of societal importance.</p>

Recent Advances on C-Se Bond-forming Reactions at Low and Room Temperature

2020 ◽  
Vol 23 (28) ◽  
pp. 3206-3225 ◽  
Author(s):  
Amol D. Sonawane ◽  
Mamoru Koketsu
Keyword(s):  
Room Temperature ◽  
Bond Formation ◽  
Bond Forming ◽  
Material Chemistry ◽  
Recent Advances ◽  
Bond Forming Reactions ◽  
Bond Formation Reactions

: Over the last decades, many methods have been reported for the synthesis of selenium- heterocyclic scaffolds because of their interesting reactivities and applications in the medicinal as well as in the material chemistry. This review describes the recent numerous useful methodologies on C-Se bond formation reactions which were basically carried out at low and room temperature.

Graphene Oxide and Its Derivatives: Their Synthesis and Use in Organic Synthesis

2019 ◽  
Vol 23 (2) ◽  
pp. 188-204 ◽  
Author(s):  
Xiangjun Peng ◽  
Xianyun Xu ◽  
Fujiang Huang ◽  
Qian Liu ◽  
Liangxian Liu
Keyword(s):  
Graphene Oxide ◽  
Carbon Materials ◽  
Device Fabrication ◽  
Organic Reactions ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
Modern Physics ◽  
Recent Developments ◽  
Optical And Mechanical Properties ◽  
Nitrogen Double Bond

Since Geim and co-workers reported their groundbreaking experiments on graphene, research on graphene oxide (GO) and its derivatives has greatly influenced the field of modern physics, chemistry, device fabrication, material science, and nanotechnology. The unique structure and fascinating properties of these carbon materials can be ascribed to their eminent chemical, electronic, electrochemical, optical, and mechanical properties of GO and its derivatives, particularly compared to other carbon allotropes. The present Review aims to provide an overview on the recent developments in the preparation of GO and its derivatives and their applications in organic reactions. We will first outline the synthesis of GO and its derivatives. Then, we will discuss the major sections about their application as stoichiometric and catalytic oxidants in organic reactions, a particular emphasis on the carbon-carbon, carbon-oxygen, and carbon-nitrogen single bond-forming reactions, as well as carbon-oxygen and carbon-nitrogen double bond-forming reactions. Simultaneously, this Review also describes briefly transition metal supported on GO or its derivatives as a catalyst for organic reaction. Lastly, we will present an outlook of potential areas where GO and its derivatives may be expected to find utility or opportunity for further growth and study.

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

scholarly journals Borane Catalysed Cyclopropenation of Arylacetylenes

2021 ◽  
Author(s):  
Katarina Stefkova ◽  
Matthew Heard ◽  
Ayan Dasgupta ◽  
Rebecca Melen
Keyword(s):  
Catalytic Activities ◽  
Bond Forming ◽  
Bond Forming Reactions

Triarylboranes have gained substantial attention as catalysts for C–C bond forming reactions due to their remarkable catalytic activities. Herein, we report B(C6F5)3 catalysed cyclopropenation of a wide variety of arylacetylenes...

scholarly journals Site-specific Umpolung amidation of carboxylic acids via triplet synergistic catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yunyun Ning ◽  
Shuaishuai Wang ◽  
Muzi Li ◽  
Jie Han ◽  
Chengjian Zhu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Amide Bond ◽  
Coupling Reagents ◽  
Complex Molecules ◽  
Bond Forming ◽  
Synergistic Catalysis ◽  
Wide Range ◽  
Amidation Reaction ◽  
Forming Methods

AbstractDevelopment of catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. In this paper, we disclose an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by the triplet synergistic catalysis of FeI2, P(V)/P(III) and photoredox catalysis, which avoids the production of byproducts from stoichiometric coupling reagents. A wide range of carboxylic acids, including aliphatic, aromatic and alkenyl acids participate smoothly in such reactions, generating structurally diverse amides in good yields (86 examples, up to 97% yield). This Umpolung amidation strategy opens a method to address challenging regioselectivity issues between nucleophilic functional groups, and complements the functional group compatibility of the classical amidation protocols. The synthetic robustness of the reaction is demonstrated by late-stage modification of complex molecules and gram-scale applications.

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