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.

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.

Sulfuryl Fluoride Promoted Thiocyanation of Alcohols: A Practical Method for Preparing Thiocyanates

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1413-1417
Author(s):  
Chengrong Ding ◽  
Guofu Zhang ◽  
Lidi Xuan ◽  
Yiyong Zhao
Keyword(s):  
Ethyl Acetate ◽  
Functional Group ◽  
High Efficiency ◽  
Bond Cleavage ◽  
Ammonium Thiocyanate ◽  
Practical Method ◽  
Sulfuryl Fluoride ◽  
Mild Conditions ◽  
One Step ◽  
The One

A novel SO2F2-promoted thiocyanation method for the one-step synthesis of thiocyanates through C–O bond cleavage of readily available alcohols with ammonium thiocyanate as the thiocyanating agent was developed. The method avoids the use of additional catalyst, and a variety of (hetero)arene, alkene and aliphatic alcohols reacted with high efficiency in ethyl acetate under mild conditions to afford the corresponding thiocyanates in excellent to quantitative yields with broad functional-group compatibility.

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.

Nickel-Catalyzed Reductive Monofluoroakylation of Alkyl Tosylate with Bromofluoromethane to Access Primary Alkyl Fluoride

2021 ◽  
Author(s):  
Ru Cui ◽  
Jie Sheng ◽  
Bing-Bing Wu ◽  
Duo-Duo Hu ◽  
Hong-Qian Zheng ◽  
...  
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Low Cost ◽  
Raw Material ◽  
Mild Conditions

A nickel-catalysed direct terminal monofluormethlyation between alkyl tosylates and a low-cost, industrial raw material bromofluoromethane has been developed. This transformation has demonstrated high efficiency, mild conditions, and good functional-group compatibility....

scholarly journals Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN2 pincer ligand

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingjie Zhang ◽  
Di Qi ◽  
Chenchen Jiao ◽  
Xiaopan Liu ◽  
Guisheng Zhang
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Materials Science ◽  
Alkylating Agents ◽  
Sonogashira Coupling ◽  
Pincer Ligand ◽  
One Pot ◽  
Mild Conditions ◽  
Alkyl Amines ◽  
Sonogashira Reactions

AbstractAlkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals.

Copper-Catalyzed Decarboxylative N-Arylation of Indole-2-carboxylic Acids

Synthesis ◽  
2019 ◽  
Vol 51 (08) ◽  
pp. 1803-1808 ◽  
Author(s):  
Yan Zhang ◽  
Zhe-Yao Hu ◽  
Xin-Chang Li ◽  
Xun-Xiang Guo
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Aryl Halides ◽  
Synthetic Method ◽  
Alternative Route ◽  
Reaction Proceeds ◽  
High Yields

A novel decarboxylative N-arylation of indole-2-carboxylic acids with aryl halides is developed. The reaction proceeds efficiently in the presence of Cu2O as the catalyst to give the corresponding N-aryl indoles in high yields. This synthetic method shows good functional group tolerance and offers an alternative route to construct N-aryl indoles.

Direct catalytic synthesis of densely substituted 3-formylpyrroles from imines and 1,4-ketoaldehydes

RSC Advances ◽  
2014 ◽  
Vol 4 (65) ◽  
pp. 34548-34551 ◽  
Author(s):  
Indresh Kumar ◽  
Nisar A. Mir ◽  
Panduga Ramaraju ◽  
Deepika Singh ◽  
Vivek K. Gupta ◽  
...  
Keyword(s):  
Room Temperature ◽  
Catalytic Synthesis ◽  
Mild Conditions ◽  
High Yields

An organocatalytic formal [3 + 2] cycloaddition have been developed between 1,4-ketoaldehydes and imines to synthesize densely substituted 3-formylpyrroles in high yields (up to 70%) under mild conditions at room temperature.

scholarly journals Efficient one-pot, four-component synthesis of N,N-dibenzyl-N-{1-[5-(3-aryl)-1,3,4-oxadiazol-2-yl]cyclobutyl}amine derivatives from the reaction of (isocyanoimino)triphenylphosphorane, dibenzylamine, an aromatic carboxylic acid and cyclobutanone

2012 ◽  
Vol 77 (9) ◽  
pp. 1175-1180 ◽  
Author(s):  
Nahid Shajari ◽  
Reza Kazemizadeh ◽  
Ali Ramazani
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Aromatic Carboxylic Acid ◽  
One Pot ◽  
Aromatic Carboxylic Acids ◽  
High Yields ◽  
Neutral Conditions

Four-component reaction of cyclobutanone, dibenzylamine and (Nisocyanimino) triphenylphosphorane in the presence of aromatic carboxylic acids proceed smoothly at room temperature and under neutral conditions to afford N,N-dibenzyl-N-{1-[5-(3-aryl)-1,3,4-oxadiazol-2-yl]cyclobutyl}amine derivatives in high yields.

Catalytic activity of dithioic acid copper complexes in the alkyne–azide cycloaddition

2013 ◽  
Vol 91 (4) ◽  
pp. 292-299 ◽  
Author(s):  
Bayardo E. Velasco ◽  
Gustavo López-Téllez ◽  
Nelly González-Rivas ◽  
Iván García-Orozco ◽  
Erick Cuevas-Yañez
Keyword(s):  
Catalytic Activity ◽  
Copper Complex ◽  
Copper Complexes ◽  
Functional Group ◽  
High Efficiency ◽  
High Catalytic Activity ◽  
Different Temperatures ◽  
High Yields

Diverse dithioic acid copper complexes exhibit a high catalytic activity in the copper-catalyzed alkyne–azide cycloaddition using several solvents under different temperatures, showing a high efficiency with only 0.005 mmol catalyst/mmol alkyne or less. A dithioic acid copper complex derived from acetophenone was selected and used as the catalyst in the preparation of a library of 1,4-disubstituted-1,2,3-triazoles. This process occurred in high yields and good functional group tolerance.

Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1373-1377 ◽  
Author(s):  
Chengrong Ding ◽  
Guofu Zhang ◽  
Yidong Yu ◽  
Yiyong Zhao ◽  
Xiaoqiang Xie
Keyword(s):  
Functional Group ◽  
Oxidative Cyclization ◽  
Mild Conditions ◽  
Broad Scope ◽  
Oxadiazole Derivatives ◽  
High Yields

A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O2.

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