Pd-Catalyzed 1,2-diarylation of vinylarenes at ambient temperature

2017 ◽  
Vol 4 (7) ◽  
pp. 1224-1228 ◽  
Author(s):  
Zhijie Kuang ◽  
Kai Yang ◽  
Qiuling Song
Keyword(s):  
Organic Chemistry ◽  
Ambient Temperature ◽  
Medicinal Chemistry ◽  
Materials Science ◽  
Biologically Relevant ◽  
Three Components

An efficient Pd-catalyzed three components reaction involving the 1,2-diarylation of vinylarenes has been disclosed. This reaction introduces two different aryl groups across vinylarenes at ambient temperature giving rise to multi-aryl substituted ethanes which are biologically relevant compounds prevailing in organic chemistry, medicinal chemistry and materials science.

Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 673-687 ◽  
Author(s):  
Yan-Ping Meng ◽  
Shi-Meng Wang ◽  
Wan-Yin Fang ◽  
Zhi-Zhong Xie ◽  
Jing Leng ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Click Chemistry ◽  
Exchange Reaction ◽  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Materials Science ◽  
Click Reaction ◽  
Chemical Properties ◽  
Chemical Transformations ◽  
Absolute Reliability

The sulfur(VI) fluoride exchange reaction (SuFEx), developed by Sharpless and co-workers in 2014, is a new category of click reaction that creates molecular connections with absolute reliability and unprecedented efficiency through a sulfur(VI) hub. Ethenesulfonyl fluoride (ESF), as one of the most important sulfur(VI) hubs, exhibits extraordinary reactivity in SuFEx click chemistry and organic synthesis. This review summarizes the chemical properties and applications of ESF in click chemistry, organic chemistry, materials science, medicinal chemistry and in many other fields related to organic synthesis.1 Introduction2 Chemical Transformations of ESF3 Chemical Transformations of 2-Arylethenesulfonyl Fluorides4 Novel SuFEx Reagents Derived from ESF5 Applications of ESF Derivatives in Medicinal Chemistry6 Applications of ESF Derivatives in Materials Science7 Conclusion

Synthesis of Monofluoroalkenes: A Leap Forward

Synthesis ◽  
2018 ◽  
Vol 50 (05) ◽  
pp. 881-955 ◽  
Author(s):  
Jean-François Paquin ◽  
Myriam Drouin ◽  
Jean-Denys Hamel
Keyword(s):  
Organic Chemistry ◽  
Medicinal Chemistry ◽  
Materials Science ◽  
Substitution Pattern ◽  
Reaction Type ◽  
Recent Advances

Monofluoroalkenes have found wide application in organic chemistry, medicinal chemistry, and materials science. This review summarizes the most recent advances made regarding the preparation of monofluoroalkenes, covering the period between October 2010 and September 2017. This review is divided in three main parts, one for each possible substitution pattern, namely di-, tri-, and tetrasubstituted. Then, for each class, further subclassification is made according to the reaction type.1 Introduction2 Disubstituted Monofluoroalkenes2.1 Disubstituted α-Monofluoroalkenes2.2 Disubstituted β-Monofluoroalkenes3 Trisubstituted Monofluoroalkenes4 Tetrasubstituted Monofluoroalkenes5 Conclusions

A Revised Modular Approach to D8-THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Author(s):  
Victor Bloemendal ◽  
Floris P. J. T. Rutjes ◽  
Thomas J. Boltje ◽  
Daan Sondag ◽  
Hidde Elferink ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Modular Approach ◽  
Coupling Reactions ◽  
One Pot ◽  
Biologically Relevant ◽  
Cross Coupling Reactions ◽  
Chemistry Research

<p>In this manuscript we describe a modular pathway to synthesize biologically relevant (–)-<i>trans</i>-Δ<sup>8</sup>-THC derivatives, which can be used to modulate the pharmacologically important CB<sub>1</sub> and CB<sub>2</sub> receptors. This pathway involves a one-pot Friedel-Crafts alkylation/cyclization protocol, followed by Suzuki-Miyaura cross-coupling reactions and gives rise to a series of new Δ<sup>8</sup>-THC derivatives. In addition, we demonstrate using extensive NMR evidence that similar halide-substituted Friedel-Crafts alkylation/cyclization products in previous articles were wrongly assigned as the para-isomers, which also has consequence for the assignment of the subsequent cross-coupled products and interpretation of their biological activity. </p> <p>Considering the importance of the availability of THC derivatives in medicinal chemistry research and the fact that previously synthesized compounds were wrongly assigned, we feel this research is describing a straightforward pathway into new cannabinoids.</p>

scholarly journals Enantioselective organocatalysis in the synthesis of biologically relevant compounds

2016 ◽  
Author(s):  
Lukasz Albrecht
Keyword(s):  
Organic Chemistry ◽  
Amino Acids ◽  
Organic Molecules ◽  
Asymmetric Induction ◽  
Chiral Catalyst ◽  
Biologically Relevant ◽  
Enantioselective Reactions ◽  
Asymmetric Organocatalysis ◽  
Biologically Relevant Molecules ◽  
Operational Simplicity

The development of methods for the preparation of biologically relevant compounds in an enantiomerically enriched form constitutes one of the most significant tasks in the contemporary organic chemistry. In particular, enantioselective reactions where prochiral substrates are converted into enantiomerically enriched products in the presence of chiral catalyst are of great importance. Recently, asymmetric organocatalysis, where simple organic molecules are used as catalysts of various enantiodifferentiating reactions, has become a highly useful synthetic tool enabling for the efficient asymmetric induction based on diverse activation modes. Herein, we report our studies on organocatalytic, enantioselective strategies for the synthesis of biologically relevant molecules such as: quaternary α-amino acids and their isoelectronic analogs α-aminophosphonates, benzo[1,5]oxazocines, α-methylidene-δ-lactones, α-alkylidene-ketones, furfural derivatives, and benzothiophenes. The devised approaches utilize readily available chiral organocatalysts to control stereo-chemical reaction outcomes. Operational simplicity, efficiency and high enantio- and diastereoselectivities are the main benefits of the developed strategies.

Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Synthesis ◽  
2021 ◽  
Author(s):  
Leonid Fershtat ◽  
Fedor Teslenko
Keyword(s):  
Transition Metal ◽  
Medicinal Chemistry ◽  
Materials Science ◽  
State Of The Art ◽  
Short Review ◽  
Advanced Materials ◽  
Metal Free ◽  
Recent Advances ◽  
Application Potential ◽  
Metal Catalyzed

Five-membered heterocyclic N-oxides attracted special attention due to their strong application potential in medicinal chemistry and advanced materials science. In this regard, novel methods for their synthesis and functionalization are constantly required. In this short review, recent state-of-the-art achievements in the chemistry of isoxazoline N-oxides, 1,2,3-triazole 1-oxides and 1,2,5-oxadiazole 2-oxides are briefly summarized. Main routes to transition-metal-catalyzed and metal-free functionalization protocols along with mechanistic considerations are outlined. Transformation patterns of the hetarene N-oxide rings as precursors to other nitrogen heterocyclic systems are also presented.

Synthesis, Photophysical and Supramolecular Properties of a π-Conjugated Molecular Crown Containing a Pentagonal Unit: A Model Compound for Fullerene C240

Synthesis ◽  
2020 ◽  
Vol 52 (17) ◽  
pp. 2535-2540
Author(s):  
Pingwu Du ◽  
Qiang Huang ◽  
Yayu Wu ◽  
Yu Zhou ◽  
Huiqing Liu ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Mass Spectrometry ◽  
Total Synthesis ◽  
Model Compound ◽  
Materials Science ◽  
Emission Spectra ◽  
Fullerene C60 ◽  
Bottom Up ◽  
Carbon Onion ◽  
Significant Challenge

The total synthesis of carbon onions is a significant challenge in the fields of materials science and organic chemistry. To date, the synthesis of even a fragment of fullerene C240 and its smallest carbon onion C60@C240 remains poorly explored. Herein, we demonstrate a bottom-up strategy to produce a novel π-extended molecular crown-shaped molecule (MC3) containing curved pentagonal and hexagonal units. This molecular crown represents a curved model compound for fullerene C240 and is fully characterized by NMR, mass spectrometry, UV-vis absorption, and from its emission spectra. Its supramolecular host–guest interaction with fullerene C60 is also investigated. MC3 and C60@MC3 can potentially be employed as seeds or templates for the bottom-up synthesis of fullerene C240 and the carbon onion C60@C240, respectively.

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2907-2912 ◽  
Author(s):  
Kensuke Kiyokawa ◽  
Satoshi Minakata ◽  
Kenta Takemoto ◽  
Shunsuke Yahata ◽  
Takumi Kojima
Keyword(s):  
Organic Chemistry ◽  
Carboxylic Acids ◽  
Present Method ◽  
Medicinal Chemistry ◽  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Efficient Synthesis ◽  
Substitution Pattern ◽  
Unsaturated Carboxylic Acids

The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf)2, which is in situ prepared from PhI(OAc)2 and Me3SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5H)-ones or furan-2(3H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.

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