Synthesis of seven-membered heterocycles via copper-catalyzed cross-coupling of terminal alkynes with diazo compounds and sequential Michael addition

2017 ◽  
Vol 15 (25) ◽  
pp. 5272-5274 ◽  
Author(s):  
Shenghu Yan ◽  
Shengyu Cao ◽  
Jiangtao Sun
Keyword(s):  
Michael Addition ◽  
Cross Coupling ◽  
Diazo Compounds ◽  
Terminal Alkynes ◽  
One Pot ◽  
Novel Approach

A novel approach to synthesize seven-membered heterocycles is established by reacting amide tethered terminal alkynes with aryl diazoacetates in a one-pot reaction.

Recent Advances in the Tandem Cyclization/Cycloaddition of Allene Intermediates from Copper-Catalyzed Cross-Coupling of Diazo Compounds with Terminal Alkynes

Synthesis ◽  
2020 ◽  
Author(s):  
Shiyong Peng ◽  
Nuan Chen ◽  
Min He ◽  
Ting Zhou ◽  
Yuqi Zhu ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Short Review ◽  
Diazo Compounds ◽  
Terminal Alkynes ◽  
Recent Advances ◽  
Recent Developments ◽  
Tandem Cyclization ◽  
Cyclic Compounds

AbstractThis short review summarizes the most recent developments (since 2010) in the tandem cyclization/cycloaddition of allene intermediates­, generated from the copper-catalyzed cross-coupling of diazo compounds with terminal alkynes, to afford cyclic compounds.1 Introduction2 Cyclization2.1 Cyclization with Nucleophiles2.2 Cyclization with Electrophiles2.3 6π-Electrocyclization2.4 Other Cyclization3 Cycloaddition4 Conclusion

Stereoselective α-indolylation of enals via an organocatalytic formal cross-coupling with indoles

2015 ◽  
Vol 13 (33) ◽  
pp. 8869-8874 ◽  
Author(s):  
Yang Hu ◽  
Lei Ju ◽  
Lin Lu ◽  
Hongmei Ma ◽  
Xinhong Yu
Keyword(s):  
Michael Addition ◽  
Cross Coupling ◽  
Cascade Process ◽  
One Pot ◽  
Nucleophilic Rearrangement ◽  
Great Simplicity

A novel organocatalytic one-pot cascade bromination–Michael addition dearomatization–nucleophilic rearrangement aromatization cascade process for the direct α-indolylation of unfunctionalized enals from readily available indoles with good yields and high E selectivity has been developed with great simplicity and practicality.

scholarly journals Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach

2014 ◽  
Vol 10 ◽  
pp. 1759-1764 ◽  
Author(s):  
Barbara Palka ◽  
Angela Di Capua ◽  
Maurizio Anzini ◽  
Gyté Vilkauskaité ◽  
Algirdas Šačkus ◽  
...  
Keyword(s):  
Multicomponent Reaction ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
One Pot ◽  
Silver Triflate ◽  
Microwave Assisted ◽  
Spectroscopic Investigations ◽  
Coupling Conditions ◽  
Substituted 1

A straightforward synthesis of 6-substituted 1-phenyl-3-trifluoromethyl-1H-pyrazolo[4,3-c]pyridines and the corresponding 5-oxides is presented. Hence, microwave-assisted treatment of 5-chloro-1-phenyl-3-trifluoromethylpyrazole-4-carbaldehyde with various terminal alkynes in the presence of tert-butylamine under Sonogashira-type cross-coupling conditions affords the former title compounds in a one-pot multicomponent procedure. Oximes derived from (intermediate) 5-alkynyl-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehydes were transformed into the corresponding 1H-pyrazolo[4,3-c]pyridine 5-oxides by silver triflate-catalyzed cyclization. Detailed NMR spectroscopic investigations (1H, 13C, 15N and 19F) were undertaken with all obtained products.

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>

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>

scholarly journals Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes

2021 ◽  
Author(s):  
Mingyu Liu ◽  
Tianhua Tang ◽  
Omar Apolinar ◽  
Rei Matsuura ◽  
Carl A. Busacca ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes
Sign in / Sign up

Export Citation Format

Share Document