scholarly journals Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester

2012 ◽  
Vol 8 ◽  
pp. 606-612 ◽  
Author(s):  
Sarah L Harding ◽  
Sebastian M Marcuccio ◽  
G Paul Savage
Keyword(s):  
Boronic Acid ◽  
Acid Ester ◽  
Nitrile Oxide ◽  
Hypervalent Iodine ◽  
Cycloaddition Reactions ◽  
Subsequent Reaction ◽  
Boronate Ester

An aryl substrate with dual functionality consisting of a nitrile oxide and a pinacolyl boronate ester was prepared by mild hypervalent iodine oxidation (diacetoxyiodobenzene) of the corresponding aldoxime, without decomposition of the boronate functionality. The nitrile oxide was trapped in situ with a variety of dipolarophiles to yield aryl isoxazolines with the boronate ester function intact and available for subsequent reaction.

Hypervalent-Iodine Mediated One-Pot Synthesis of Isoxazolines and Isoxazoles bearing Difluoromethyl Phosphonate Moiety

2021 ◽  
Author(s):  
Romana Pajkert ◽  
Henryk Koroniak ◽  
Pawel Kafarski ◽  
Gerd Volker Roeschenthaler
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Hypervalent Iodine ◽  
One Pot ◽  
One Pot Synthesis

A one-pot, regioselective 1,3-dipolar cycloaddition of in situ generated (diethoxyphosphoryl)difluoromethyl nitrile oxide toward selected alkenes and alkynes is reported. This protocol enables facile access to 3,5-disubstituted isoxazolines and isoxazoles bearing...

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

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2299-2310 ◽  
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

π-Facial Selectivity in 1,3-Dipolar Cycloaddition Reactions of α-Methylidene-γ-lactone Substituted by 4-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl Group in γ-Position

2002 ◽  
Vol 67 (3) ◽  
pp. 353-364 ◽  
Author(s):  
Petr Melša ◽  
Ctibor Mazal
Keyword(s):  
Double Bond ◽  
Carboxylic Acid ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Enantiomerically Pure ◽  
Nitrile Imine ◽  
Facial Selectivity ◽  
Excellent Selectivity

Diastereoselectivity of 1,3-dipolar cycloaddition reactions of benzyl azide, diazomethane, a nitrile oxide and a nitrile imine to α-methylidene-γ-lactone dipolarophile was effectively controlled by a bulky γ-substituent, 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl in γ-position of the dipolarophile. The dipoles added from the less hindered face of the double bond with an excellent selectivity. Enantiomerically pure dipolarophile was prepared from the easily available (S)-5-oxotetrahydrohydrofuran-2-carboxylic acid.

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

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

Hypervalent iodine catalysis for selective oxidation of Baylis–Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone

2016 ◽  
Vol 40 (12) ◽  
pp. 10300-10304 ◽  
Author(s):  
Raktani Bikshapathi ◽  
Parvathaneni Sai Prathima ◽  
Vaidya Jayathirtha Rao
Keyword(s):  
Selective Oxidation ◽  
Carbonyl Compounds ◽  
Hypervalent Iodine ◽  
In Situ Generation ◽  
Iodosobenzoic Acid ◽  
High Yields

An efficient, eco-friendly protocol for selective oxidation of primary and secondary Baylis–Hillman alcohols to the corresponding carbonyl compounds in high yields has been developed with 2-iodosobenzoic acid (IBA).

Direct oxidative cyanation of tertiary amines promoted by in situ generated hypervalent iodine(III)-CN intermediate

2015 ◽  
Vol 56 (41) ◽  
pp. 5628-5631 ◽  
Author(s):  
Hang Shen ◽  
Xiaohui Zhang ◽  
Qing Liu ◽  
Jing Pan ◽  
Wen Hu ◽  
...  
Keyword(s):  
Hypervalent Iodine ◽  
Tertiary Amines

Symmetrical tetra-β″-sulfoleno-meso-aryl-porphyrins — synthesis, spectroscopy and structural characterization

2014 ◽  
Vol 18 (01n02) ◽  
pp. 115-122 ◽  
Author(s):  
Srinivas Banala ◽  
Klaus Wurst ◽  
Bernhard Kräutler
Keyword(s):  
Metal Complexes ◽  
Crystal Structures ◽  
Structural Characterization ◽  
Building Blocks ◽  
Cycloaddition Reactions ◽  
One Pot

We report here the preparation (in "one-pot") of a tetra-β″-sulfoleno-meso-aryl-porphyrin in about 80% yield by using an optimized modification of Lindsey's variant of the Adler–Longo approach. The Zn ( II )-, Cu ( II )- and Ni ( II )-complexes of the symmetrical porphyrin were prepared and characterized spectroscopically. Crystal structures of the fluorescent Zn ( II )- and of the non-fluorescent Ni ( II )-tetra-β″-sulfoleno-meso-aryl-porphyrinates showed the highly substituted porphyrin ligands to be nearly perfectly planar. The Zn ( II )-complex of this porphyrin has been used as a thermal precursor of a reactive diene, and — formally — of lateral and diagonal bis-dienes, of a tris-diene and of a tetra-diene, which all underwent [4 + 2]-cycloaddition reactions in situ with a range of dienophiles. Thus, the tetra-β″-sulfoleno-meso-aryl-porphyrin and its metal complexes represent reactive building blocks, "programmed" for the syntheses of symmetrical and highly functionalized porphyrins.

Radiosynthesis of [11C]Carboxamides via Reaction of [11C]CO2Captured by a Cu(I)-Based Catalyst System with Boronic Acid Ester Precursors

2015 ◽  
pp. 197-205
Author(s):  
Patrick J. Riss ◽  
Shuiyu Lu ◽  
Sanjay Telu ◽  
Franklin I. Aigbirhio ◽  
Victor W. Pike
Keyword(s):  
Boronic Acid ◽  
Acid Ester ◽  
Catalyst System

The aryl iodine-catalyzed organic transformation via hypervalent iodine species generated in situ

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Xuemin Li ◽  
Guangchen Li ◽  
Yifu Cheng ◽  
Yunfei Du
Keyword(s):  
Organic Synthesis ◽  
Oxidative Coupling ◽  
Hypervalent Iodine ◽  
Organic Transformations ◽  
Aryl Iodide ◽  
Oxidative Reaction ◽  
Iodine Species ◽  
Iodine Chemistry

Abstract The application of hypervalent iodine species generated in situ in organic transformations has emerged as a useful and powerful tool in organic synthesis, allowing for the construction of a series of bond formats via oxidative coupling. Among these transformations, the catalytic aryl iodide can be oxidized to hypervalent iodine species, which then undergoes oxidative reaction with the substrates and the aryl iodine regenerated again once the first cyclic cycle of the reaction is completed. This review aims to systematically summarize and discuss the main progress in the application of in situ-generated hypervalent iodine species, providing references and highlights for synthetic chemists who might be interested in this field of hypervalent iodine chemistry.

Hypervalent Iodine(III)-Catalyzed Epoxidation of β-Cyanostyrenes

Synthesis ◽  
2019 ◽  
Vol 51 (23) ◽  
pp. 4473-4486 ◽  
Author(s):  
Saeesh R. Mangaonkar ◽  
Fateh V. Singh
Keyword(s):  
Reaction Time ◽  
Room Temperature ◽  
Hypervalent Iodine ◽  
Short Reaction Time ◽  
Convenient Approach

A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 mol% PhI as precatalyst in the presence of 2.0 equivalents Oxone as an oxidant and 2.4 equivalents of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time.

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