A practical and efficient route to heteraphanes: synthesis of structurally simplified analogues of ansamycins

The intramolecular Mitsunobu reaction has been employed for the practical synthesis of a wide variety of heteraphanes. This strategy enabled the efficient synthesis of a diverse range of macrocycles with varying ring sizes under mild conditions.

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Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

Molecules ◽

10.3390/molecules26071897 ◽

2021 ◽

Vol 26 (7) ◽

pp. 1897

Author(s):

Hideyasu China ◽

Nami Kageyama ◽

Hotaka Yatabe ◽

Naoko Takenaga ◽

Toshifumi Dohi

Keyword(s):

Aqueous Solution ◽

Room Temperature ◽

Practical Method ◽

Hypervalent Iodine ◽

Mild Conditions ◽

Sequential Procedures ◽

Iodine Compounds ◽

Practical Synthesis ◽

Iodosobenzoic Acid ◽

Lower Temperature

We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone® in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.

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Design of bifunctional quaternary phosphonium salt catalysts for CO2 fixation reaction with epoxides under mild conditions

Green Chemistry ◽

10.1039/c6gc01630h ◽

2016 ◽

Vol 18 (17) ◽

pp. 4611-4615 ◽

Cited By ~ 75

Author(s):

Shiyao Liu ◽

Naoki Suematsu ◽

Keiji Maruoka ◽

Seiji Shirakawa

Keyword(s):

Co2 Fixation ◽

Phosphonium Salt ◽

Cyclic Carbonates ◽

Efficient Synthesis ◽

Reaction Conditions ◽

Mild Conditions ◽

Phosphonium Iodide ◽

Fixation Reaction ◽

Quaternary Phosphonium Salt

An efficient synthesis of cyclic carbonates from epoxides and CO2 under mild reaction conditions was achieved via the use of a designed bifunctional quaternary phosphonium iodide catalyst.

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Oxidation of 2-methylpyrroles with perchlorinated iron(III) metalloporphyrin catalysts: a versatile synthesis of symmetric and asymmetric dipyrromethanes

Canadian Journal of Chemistry ◽

10.1139/v98-190 ◽

1998 ◽

Vol 76 (10) ◽

pp. 1467-1473 ◽

Cited By ~ 2

Author(s):

Veranja Karunaratne ◽

David Dolphin

Keyword(s):

Catalytic Oxidation ◽

Allylic Alcohols ◽

The Novel ◽

Efficient Synthesis ◽

Mild Conditions ◽

Metalloporphyrin Catalysts

A variety of substituted 2-methylpyrroles (3-8) were oxidized using the metalloporphyrin catalysts iron(III) meso-tetra(2,6-dichloro-3-sulphonatophenyl)-β-octachloroporphyrin chloride 1 and iron(III) meso-tetra(2,6-dichlorophenyl)-β-octachloroporphyrin chloride 2 under very mild conditions. Treatment of the resulting allylic alcohols 3a-8a with α-free pyrroles 9 and 10 resulted in a very efficient synthesis of the corresponding dipyrromethanes 3b-8b and 3c-8c. Furthermore, the above allylic alcohols when treated with furfurylamine produced the novel (2-furylmethyl)-2-pyrrolylmethylamines 3d-8d.Key words: catalytic oxidation, metalloporphyrins, pyrroles, dipyrromethanes, polyhalogenated porphyrins.

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Efficient synthesis of unsymmetrical heteroaryl thioethers and chalcogenides by alkali hydroxide-mediated SNAr reactions of heteroaryl halides and dichalcogenides

RSC Advances ◽

10.1039/c6ra10517c ◽

2016 ◽

Vol 6 (62) ◽

pp. 56930-56935 ◽

Cited By ~ 14

Author(s):

Xiantao Ma ◽

Quan Liu ◽

Xiaojuan Jia ◽

Chenliang Su ◽

Qing Xu

Keyword(s):

Efficient Synthesis ◽

Practical Synthesis ◽

Alkali Hydroxide

An efficient SNAr reaction of heteroaryl halides and diorganyl dichalcogenides is developed for practical synthesis of the useful unsymmetrical heteroaryl thioethers and chalcogenides.

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ChemInform Abstract: Facile and Efficient Synthesis of 1-Haloalkynes via DBU-Mediated Reaction of Terminal Alkynes and N-Haloimides under Mild Conditions.

ChemInform ◽

10.1002/chin.201507081 ◽

2015 ◽

Vol 46 (7) ◽

pp. no-no

Author(s):

Mengru Li ◽

Yueju Li ◽

Baozhong Zhao ◽

Fushun Liang ◽

Long-Yi Jin

Keyword(s):

Terminal Alkynes ◽

Efficient Synthesis ◽

Mild Conditions

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Efficient synthesis of enantiomerically pure (S)-δ-azaproline starting from (R)-α-hydroxy-γ-butyrolactone via the Mitsunobu reaction

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2009.07.003 ◽

2009 ◽

Vol 20 (15) ◽

pp. 1809-1812 ◽

Cited By ~ 5

Author(s):

Emelyne Voss ◽

Axelle Arrault ◽

Jacques Bodiguel ◽

Brigitte Jamart-Grégoire

Keyword(s):

Mitsunobu Reaction ◽

Efficient Synthesis ◽

Enantiomerically Pure

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ChemInform Abstract: Efficient Synthesis of 2-Methylaminothiazolines via Mitsunobu Reaction of N-(2-Hydroxyethyl)-N′-methyl-thioureas.

ChemInform ◽

10.1002/chin.199928163 ◽

2010 ◽

Vol 30 (28) ◽

pp. no-no

Author(s):

Taek Hyeon Kim ◽

Mi-Hyun Cha

Keyword(s):

Mitsunobu Reaction ◽

Efficient Synthesis

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Efficient Synthesis of 3,4-Disubstituted 7-Azaindoles Employing SEM as a Dual Protecting–Activating Group

Synlett ◽

10.1055/s-0039-1690735 ◽

2019 ◽

Vol 30 (20) ◽

pp. 2273-2278 ◽

Cited By ~ 1

Author(s):

Piroska Gyárfás ◽

János Gerencsér ◽

Warren S. Wade ◽

László Ürögdi ◽

Zoltán Novák ◽

...

Keyword(s):

Functional Groups ◽

Efficient Method ◽

Reaction Times ◽

Nucleophilic Aromatic Substitution ◽

Aromatic Substitution ◽

Efficient Synthesis ◽

Mild Conditions

An efficient method for nucleophilic aromatic substitution on 7-azaindoles has been developed. The reaction is facilitated by the unique dual influence of SEM as both protecting and activating group, permitting mild conditions and short reaction times that are compatible with sensitive functional groups. The method is suitable for the synthesis of a broad range of products, most notably ethers.

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