Synthesis of O-Aroyl-N,N-dimethylhydroxylamines through Hypervalent Iodine-Mediated Amination of Carboxylic Acids with N,N-Dimethylformamide

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4303-4308 ◽  
Author(s):  
Dong Li ◽  
Chuancheng Zhang ◽  
Qiang Yue ◽  
Zhen Xiao ◽  
Xianglan Wang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Functional Group ◽  
Hypervalent Iodine ◽  
Electrophilic Amination ◽  
Mild Conditions

An efficient protocol for the synthesis of O-aroyl-N,N-dimethylhydroxylamines, which are important electrophilic amination reagents, is described. The reaction between carboxylic acids and N,N-dimethylformamide is mediated by hypervalent iodine and occurs under mild conditions at room temperature to give the desired products in good yields. The process shows good functional group compatibility and air and moisture tolerance.

Construction of Esters through Sulfuryl Fluoride (SO2F2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature

Synthesis ◽  
2019 ◽  
Vol 51 (20) ◽  
pp. 3901-3907 ◽  
Author(s):  
Shi-Meng Wang ◽  
Njud S. Alharbi ◽  
Hua-Li Qin
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Functional Group ◽  
High Efficiency ◽  
Sulfuryl Fluoride ◽  
Mild Conditions ◽  
High Yields

A facile method for the construction of esters through dehydrative coupling of carboxylic acids with alcohols is developed. The reactions are mediated by sulfuryl fluoride (SO2F2) at room temperature and proceed with high efficiency. The method has several advantages including broad substrate scope, mild conditions, excellent functional group compatibility and affords high yields, even on gram scale.

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

Molecules ◽  
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.

scholarly journals Mechanically induced solvent-free esterification method at room temperature

RSC Advances ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 5080-5085
Author(s):  
Lei Zheng ◽  
Chen Sun ◽  
Wenhao Xu ◽  
Alexandr V. Dushkin ◽  
Nikolay Polyakov ◽  
...  
Keyword(s):  
Natural Products ◽  
Carboxylic Acids ◽  
Late Stage ◽  
Reaction Mechanisms ◽  
Room Temperature ◽  
Solvent Free ◽  
Mild Conditions

We have developed I2/KH2PO2 and KI/P(OEt)3 strategy syntheses of esters from carboxylic acids and alcohols through different reaction mechanisms. The advantages of present protocol: mild conditions and late-stage diversification of natural products.

Electrophilic Amination with Anthranils through Thioamide-Assisted Cobalt(III)-Catalyzed C(sp3)–H Activation

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3881-3890
Author(s):  
Jie Li ◽  
Lei Liu ◽  
Zhao Zhang ◽  
Yucheng Wang ◽  
Yan Zhang
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Atom Economy ◽  
Electrophilic Amination ◽  
Amino Aldehydes ◽  
Mild Conditions ◽  
Weakly Coordinating

Cobalt(III)-catalyzed electrophilic amination of inert C(sp3)–H bonds of weakly coordinating thioamides with readily accessible anthranil derivatives was accomplished under mild conditions, with good functional group tolerance, thus providing various amino aldehydes and amino ketones. Moreover, our protocol with the versatile [Cp*Co(MeCN)3][SbF6]2 features excellent atom-economy and oxidant-free conditions, and allows facile late-stage functionalization.

scholarly journals A Versatile New Reagent for Nitrosation under Mild Conditions

2021 ◽  
Author(s):  
Jordan D. Galloway ◽  
Cristian Sarabia ◽  
James C. Fettinger ◽  
Hrant Hratchian ◽  
Ryan Baxter
Keyword(s):  
Room Temperature ◽  
Computational Analysis ◽  
Functional Group ◽  
Nitroso Compounds ◽  
Chemical Reagent ◽  
Experimental Conditions ◽  
X Ray ◽  
Mild Conditions ◽  
Rotational Isomers ◽  
First Time

We report a new chemical reagent for transnitrosation under mild experimental conditions. This new reagent is stable to air and moisture across a broad range of temperatures, and is effective for transnitrosation in multiple solvents. Compared to traditional nitrosation methods, our reagent shows high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. Several challenging nitroso-compounds are accessed here for the first time, including 15N isotopologues. X-ray data confirms two rotational isomers of the reagent are configurationally stable at room temperature, although only one isomer is effective for transnitrosation. Computational analysis describes the energetics of rotamer interconversion, including interesting geometry-dependent hybridization ef-fects.

Pd(ii) catalyzed ortho C–H iodination of phenylcarbamates at room temperature using cyclic hypervalent iodine reagents

2015 ◽  
Vol 51 (49) ◽  
pp. 10014-10017 ◽  
Author(s):  
Xiuyun Sun ◽  
Xia Yao ◽  
Chao Zhang ◽  
Yu Rao
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Hypervalent Iodine ◽  
Weak Coordination ◽  
Unique Mechanism

The first example to access ortho iodinated phenols using cyclic hypervalent iodine(iii) reagents through palladium(ii) catalyzed C–H activation has been developed via weak coordination. The reaction showed excellent regioselectivity, reactivity and good functional group tolerance. A unique mechanism was proposed.

scholarly journals Stable CAAC-based Ruthenium Complexes for Dynamic Olefin Metathesis Under Mild Conditions

2021 ◽  
Author(s):  
Oleksandr Kravchenko ◽  
Brian J.J. Timmer ◽  
Maurice Biedermann ◽  
Andrew Kentaro Inge ◽  
Olof Ramstrom
Keyword(s):  
Olefin Metathesis ◽  
High Stability ◽  
Room Temperature ◽  
Functional Group ◽  
Biologically Active ◽  
Dynamic Covalent Chemistry ◽  
Mild Conditions ◽  
Cross Metathesis ◽  
Potential Applications ◽  
Metathesis Catalysts

<p>A series of olefin metathesis catalysts bearing cyclic (alkyl)(amino)carbene (CAAC) ligands of varying size and steric demand has been synthesized and evaluated in ring-closing-, self-, and cross-metathesis reactions at room temperature. The catalysts were also probed for potential applications in dynamic covalent chemistry. The majority of the catalysts showed high stability, and remained active in the reaction mixtures for several days, including in methanol-based solutions. Higher temperatures could be used to control the reactivity towards sterically challenging substrates, enabling formation of tetrasubstituted olefins. The CAAC complexes exhibited remarkable functional group tolerance towards heteroaromatic and nucleophilic additives, making them potentially useful in the screening of biologically active compounds.</p>

scholarly journals Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

2018 ◽  
Vol 14 ◽  
pp. 1087-1094 ◽  
Author(s):  
Toshifumi Dohi ◽  
Shohei Ueda ◽  
Kosuke Iwasaki ◽  
Yusuke Tsunoda ◽  
Koji Morimoto ◽  
...  
Keyword(s):  
Organic Solvent ◽  
Carboxylic Acids ◽  
Hypervalent Iodine ◽  
Homolytic Cleavage ◽  
Radical Species ◽  
Direct Introduction ◽  
Mild Conditions ◽  
High Degree ◽  
Oxidation System

An oxidation system comprising phenyliodine(III) diacetate (PIDA) and iodosobenzene with inorganic bromide, i.e., sodium bromide, in an organic solvent led to the direct introduction of carboxylic acids into benzylic C–H bonds under mild conditions. The unique radical species, generated by the homolytic cleavage of the labile I(III)–Br bond of the in situ-formed bromo-λ3-iodane, initiated benzylic carboxylation with a high degree of selectivity for the secondary benzylic position.

Rh(iii)-Catalyzedortho-C–H alkynylation ofN-phenoxyacetamides with hypervalent iodine-alkyne reagents at room temperature

2018 ◽  
Vol 16 (1) ◽  
pp. 43-47 ◽  
Author(s):  
Sisheng Hu ◽  
Liang Lu ◽  
Tongyang Zhu ◽  
Qian Wu ◽  
Ying Chen ◽  
...  
Keyword(s):  
Room Temperature ◽  
Hypervalent Iodine ◽  
Mild Conditions ◽  
Directing Group

Directing group ONHR preservedortho-alkynylation under mild conditions catalyzed by rhodium is reported.

Access to Highly Substituted Pyrimidine N-Oxides and 4-Acetoxymethyl-Substituted Pyrimidines via the LANCA Three-Component Reaction–Cyclocondensation Sequence

Synthesis ◽  
2021 ◽  
Author(s):  
Reinhold Zimmer ◽  
Hans-Ulrich Reissig ◽  
Luise Schefzig ◽  
Timon Kurzawa ◽  
Giaime Rancan ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Hydroxylamine Hydrochloride ◽  
Trifluoroacetic Anhydride ◽  
Pyrimidine Derivatives ◽  
Mild Conditions ◽  
Structural Variety ◽  
Three Component Reaction ◽  
Sterically Demanding ◽  
Synthetic Utility

AbstractThe LANCA three-component reaction of lithiated alkoxy­allenes (LA), nitriles (N), and carboxylic acids (CA) smoothly provides β-alkoxy-β-ketoenamides in broad structural variety. The subsequent cyclocondensation of these compounds with hydroxylamine hydrochloride afforded a large library of pyrimidine N-oxides under mild conditions and in good yields. Their synthetic utility was further increased by the Boekelheide rearrangement leading to 4-acetoxymethyl-substituted pyrimidines. With trifluoroacetic anhydride the rearrangement proceeds even at room temperature and directly furnishes 4-hydroxymethyl-substituted pyrimidine derivatives. The key reactions are very robust and work well even in the presence of sterically demanding substituents.

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