Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions

1,3,5-Trisubstituted 1,3,5-triazinanes (hexahydro-1,3,5-triazines), as stable and readily available surrogates for formaldimines, have found extensive applications for the construction of various nitrogen-containing compounds. The formaldimines, formed in situ from this reagent class, can participate in various aminomethylation and cycloaddition reactions. This short review presents recent advances in this field with emphasis on the conceptual ideas behind the developed methodologies and the reaction mechanisms.1 Introduction2 Aminomethylations with 1,3,5-Triazinanes3 Cycloadditions with 1,3,5-Triazinanes3.1 Use of 1,3,5-Triazinanes as Two-Atom Synthons3.2 Use of 1,3,5-Triazinanes as Three-Atom Synthons3.3 Use of 1,3,5-Triazinanes as Four-Atom Synthons3.4 Use of 1,3,5-Triazinanes as Six-Atom Synthons4 Conclusions

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Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions

Synthesis ◽

10.1055/s-0040-1707122 ◽

2020 ◽

Vol 52 (16) ◽

pp. 2299-2310 ◽

Cited By ~ 4

Author(s):

Akira Yoshimura ◽

Akio Saito ◽

Viktor V. Zhdankin ◽

Mekhman S. Yusubov

Keyword(s):

Heterocyclic Compounds ◽

Short Review ◽

Active Species ◽

Hypervalent Iodine ◽

Cycloaddition Reactions ◽

Iodine Species ◽

Oxazole Derivatives

Organohypervalent iodine reagents are widely used for the preparation of various oxazolines, oxazoles, isoxazolines, and isoxazoles. In the formation of these heterocyclic compounds, hypervalent iodine species can serve as the activating reagents for various substrates, as well as the heteroatom donor reagents. In recent research, both chemical and electrochemical approaches toward generation of hypervalent iodine species have been utilized. The in situ generated active species can react with appropriate substrates to give the corresponding heterocyclic products. In this short review, we summarize the hypervalent-iodine-mediated preparation of oxazolines, oxazoles, isoxazolines, and isoxazoles starting from various substrates.1 Introduction2 Synthesis of Oxazolines3 Synthesis of Oxazoles4 Synthesis of Isoxazolines5 Synthesis of Isoxazoles6 Conclusion

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Recent Advances in Nickel Catalysis Enabled by Stoichiometric Metallic Reducing Agents

Synthesis ◽

10.1055/s-0036-1591853 ◽

2017 ◽

Vol 50 (03) ◽

pp. 499-513 ◽

Cited By ~ 80

Author(s):

Edward Richmond ◽

Joseph Moran

Keyword(s):

Cross Coupling ◽

Short Review ◽

Reducing Agents ◽

Nickel Catalysis ◽

Future Directions ◽

Recent Advances ◽

Reductive Carboxylation

This short review describes recent advances in the field of nickel catalysis, specifically transformations employing stable Ni(II) precatalysts that are activated in situ with the use of stoichiometric metallic reducing agents. The article seeks to summarise the field, highlighting key studies and discussing mechanistic facets. The review closes with an eye on future directions in redox-enabled nickel catalysis.1 Introduction2 Nickel Catalysis Enabled by Metallic Reducing Agents3 Reductive Cross-Coupling4 Reductive Carboxylation and Acylation-type reactions5 Miscellaneous Reactivity6 Perspectives and Future Directions

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Inter- and Intramolecular Cycloaddition Reactions of Ethenetricarboxylates with Styrenes and Halostyrenes

Synthesis ◽

10.1055/s-0040-1706547 ◽

2020 ◽

Author(s):

Shoko Yamazaki ◽

Zhichao Wang ◽

Kentaro Iwata ◽

Khotaro Katayama ◽

Hirotaka Sugiura ◽

...

Keyword(s):

Dft Calculations ◽

Reaction Mechanisms ◽

Cycloaddition Reactions ◽

Intramolecular Cycloaddition ◽

High Diversity

AbstractInter- and intramolecular cycloaddition reactions of ethenetricarboxylates with styrenes and α-halostyrenes have been investigated. The reactions of ethenetricarboxylates with styrenes or α-bromostyrenes in the presence of SnCl4 or SnBr4 stereoselectively gave 2,4-cis-substituted cyclobutanes. The intramolecular cycloaddition reactions of a series of styrene-functionalized ethenetricarboxylate amides, including in situ generated derivatives, showed high diversity of reaction modes depending on the structures and substituents of the substrates. The regioselectivity and stereoselectivity of the reactions as well as reaction mechanisms were discussed based on the DFT calculations.

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The Power of Iron Catalysis in Diazo Chemistry

Synthesis ◽

10.1055/s-0040-1707272 ◽

2020 ◽

Vol 53 (01) ◽

pp. 79-94

Author(s):

Thierry Ollevier ◽

Virginie Carreras ◽

Nour Tanbouza

Keyword(s):

Short Review ◽

Metal Catalysts ◽

Diazo Compounds ◽

Cycloaddition Reactions ◽

Insertion Reactions ◽

Iron Catalysis ◽

Recent Advances ◽

Olefination Reactions

AbstractThe use of iron catalysis to enable reactions with diazo compounds has emerged as a valuable tool to forge carbon–carbon or carbon–heteroatom bonds. While diazo compounds are often encountered with toxic and expensive metal catalysts, such as Rh, Ru, Pd, Ir, and Cu, a resurgence of Fe catalysis has been observed. This short review will showcase and highlight the recent advances in iron-mediated reactions of diazo compounds.1 Introduction2 Insertion Reactions2.1 Insertion into B–H Bonds2.2 Insertion into Si–H Bonds2.3 Insertion into N–H Bonds2.4 Insertion into S–H bonds3 Ylide Formation and Subsequent Reactions3.1 Doyle–Kirmse Rearrangement3.2 [1,2]-Stevens and Sommelet–Hauser Rearrangements3.3 Olefination Reactions3.4 Cycloaddition Reactions3.5 gem-Difluoroalkenylation4 Three-Component Reactions5 Miscellaneous6 Conclusion

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Recent Advances in Metal-Catalyzed, Electrochemical Coupling Reactions of sp2 Halides/Boronic Acids and sp3 Centers

Synthesis ◽

10.1055/s-0040-1706085 ◽

2020 ◽

Author(s):

Zachary J. Gale-Day

Keyword(s):

Cross Coupling ◽

Short Review ◽

Boronic Acids ◽

Coupling Reactions ◽

Cross Coupling Reactions ◽

Organic Electrochemistry ◽

Recent Advances ◽

Electrochemical Coupling ◽

Metal Catalyzed

AbstractTraditionally, metal-catalyzed cross-coupling reactions rely on stable but expensive metals, such as palladium. However, the recent development of synthetic organic electrochemistry allows for in situ redox manipulations, expanding the use of cheaper, abundant and sustainable metals, such as nickel and copper as efficient cross-coupling catalysts. This short review covers the recent advances in metal-catalyzed electrochemical coupling reactions, with a focus on reactions of sp2 electrophiles and nucleophiles with sp3 coupling partners to form both C–C and C–heteroatom bonds.1 Introduction2 Nickel-Catalyzed C–C sp2–sp3 Coupling Reactions3 Coupling of Aryl Groups with Heteroatomic Nuclei4 Conclusion

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Catalytic, Enantioselective Diamination of Alkenes

Synthesis ◽

10.1055/s-0040-1719822 ◽

2021 ◽

Author(s):

Scott E. Denmark ◽

Zhong-Lin Tao

Keyword(s):

Asymmetric Synthesis ◽

Reaction Mechanisms ◽

Short Review ◽

Biologically Active Compounds ◽

Biologically Active ◽

Active Compounds ◽

Recent Advances ◽

Vicinal Diamines

AbstractEnantioselective diamination of alkenes represents one of the most straightforward methods to access enantioenriched, vicinal diamines, which are not only frequently encountered in biologically active compounds, but also have broad applications in asymmetric synthesis. Although the analogous dihydroxylation of olefins is well-established, the development of enantioselective olefin diamination lags far behind. Nevertheless, several successful methods have been developed that operate by different reaction mechanisms, including a cycloaddition pathway, a two-electron redox pathway, and a radical pathway. This short review summarizes recent advances and identifies limitations, with the aim of inspiring further developments in this area.1 Introduction2 Cycloaddition Pathway3 Two-Electron Redox Pathway3.1 Pd(0)/Pd(II) Diamination3.2 Pd(II)/Pd(IV) Diamination3.3 I(I)/I(III) Diamination3.4 Se(II)/Se(IV) Diamination4 One-Electron Radical Pathway4.1 Cu-Catalyzed Diamination4.2 Fe-Catalyzed Diamination5 Summary and Outlook

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In Situ Generation of Unstable Difluoromethylphosphonate-Containing Diazoalkanes and Their Use in [3 + 2] Cycloaddition Reactions with Vinyl Sulfones

Organic Letters ◽

10.1021/acs.orglett.1c00150 ◽

2021 ◽

Vol 23 (3) ◽

pp. 1130-1134

Author(s):

Haibo Mei ◽

Li Wang ◽

Romana Pajkert ◽

Qian Wang ◽

Jingcheng Xu ◽

...

Keyword(s):

Cycloaddition Reactions ◽

In Situ Generation

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Recent advances in understanding oxygen evolution reaction mechanisms over iridium oxide

Inorganic Chemistry Frontiers ◽

10.1039/d0qi01465f ◽

2021 ◽

Author(s):

Takahiro Naito ◽

Tatsuya Shinagawa ◽

Takeshi Nishimoto ◽

Kazuhiro Takanabe

Keyword(s):

Reaction Mechanism ◽

Oxygen Evolution ◽

Oxygen Evolution Reaction ◽

Reaction Mechanisms ◽

State Of The Art ◽

Iridium Oxide ◽

The State ◽

Computational Studies ◽

Recent Advances ◽

Iridium Oxides

Recent spectroscopic and computational studies concerning the oxygen evolution reaction over iridium oxides are reviewed to provide the state-of-the-art understanding of its reaction mechanism.

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