- Br?nsted Acid Mediated Nucleophilic Functionalization of Amides through Stable Amide C?N Bond Cleavage; One-Step Synthesis of 2-Substituted Benzothiazoles
-
We have developed a Br?nsted acid mediated synthetic method to directly cleave stable amide C?N bonds by a variety of alcohol and amine nucleophiles. Reverse reactivity was observed and alcoholysis of amides by activated primary and secondary benzylic, and propargylic alcohols have been achieved instead of the expected nucleophilic substitution of alcohols. As an application, 2-substituted benzothiazole derivatives have been synthesized in one pot employing 2-aminothiophenol as nucleophile.
- Biswas, Srijit,Biswas, Subrata,Duari, Surajit,Elsharif, Asma M.,Maity, Srabani,Roy, Arnab
-
supporting information
p. 3569 - 3572
(2021/07/22)
-
- Kinetic Analysis as an Optimization Tool for Catalytic Esterification with a Moisture-Tolerant Zirconium Complex
-
This work describes the use of kinetics as a tool for rational optimization of an esterification process with down to equimolar ratios of reagents using a recyclable commercially available zirconocene complex in catalytic amounts. In contrast to previously reported group IV metal-catalyzed esterification protocols, the work presented herein circumvents the use of water scavengers and perfluorooctane sulfonate (PFOS) ligands. Insights into the operating mechanism are presented.
- Dalla-Santa, Oscar,Lundberg, Helena,Szabó, Zoltán,Villo, Piret
-
p. 6959 - 6969
(2020/06/27)
-
- Sodium cyanide-promoted copper-catalysed aerobic oxidative synthesis of esters from aldehydes
-
A simple and efficient copper-catalysed procedure for oxidative esterification of aldehydes with alcohols and phenols mediated by sodium cyanide, using air as a clean oxidant, is described. A variety of aromatic aldehydes and structurally different alcohols and phenols reacted efficiently, and the product esters were obtained in good to excellent yields under normal atmospheric and solvent-free conditions.
- Nowrouzi, Najmeh,Abbasi, Mohammad,Bagheri, Maryam
-
-
- Efficient and selective esterification of aromatic aldehydes with alcohols (1:1) using air as the simplest available oxidant and KCN
-
A new and efficient method is described for the oxidative esterification of aromatic aldehydes with different types of alcohols such as primary, secondary, benzylic, allylic and cyclic alcohols and phenols using air as the simplest available oxidant and potassium cyanide in DMF under neutral conditions in high yields. The present method esterifies aldehydes with alcohols in 1:1 molar ratio with excellent chemoselectivity and avoids the use of an external oxidant beside 02 from air.
- Aghapour, Ghasem,Karimzadeh, Maryam
-
p. 1013 - 1018
(2017/11/10)
-
- Cu(ii)-catalyzed esterification reaction via aerobic oxidative cleavage of C(CO)-C(alkyl) bonds
-
A novel Cu(ii)-catalyzed aerobic oxidative esterification of simple ketones for the synthesis of esters has been developed with wide functional group tolerance. This process is assumed to go through a tandem sequence consisting of α-oxygenation/esterification/nucleophilic addition/C-C bond cleavage and carbon dioxide is released as the only byproduct.
- Ma, Ran,He, Liang-Nian,Liu, An-Hua,Song, Qing-Wen
-
supporting information
p. 2145 - 2148
(2016/02/09)
-
- A novel nickel-catalyzed synthesis of thioesters, esters and amides from aryl iodides in the presence of chromium hexacarbonyl
-
This study describes our findings on a novel and cheap NiCl2 catalytic system under ligand-free conditions for the efficient thiocarbonylation, alkoxycarbonylation and amidocarbonylation reactions of aryl iodides in the presence of Cr(CO)6 as the solid source of carbon monoxide under air. A variety of aryl iodides tolerated the reaction conditions and structurally different thiols, alcohols and amines were used efficiently. The corresponding thioesters, esters and amides were obtained in good to excellent yield at atmospheric pressure under mild reaction conditions.
- Iranpoor, Nasser,Firouzabadi, Habib,Etemadi-Davan, Elham,Nematollahi, Arash,Firouzi, Hamid Reza
-
p. 6445 - 6452
(2015/08/11)
-
- From ketones to esters by a Cu-catalyzed highly selective C(CO)-C(alkyl) bond cleavage: Aerobic oxidation and oxygenation with air
-
The Cu-catalyzed aerobic oxidative esterification of simple ketones via C-C bond cleavage has been developed. Varieties of common ketones, even inactive aryl long-chain alkyl ketones, are selectively converted into esters. The reaction tolerates a wide range of alcohols, including primary and secondary alcohols, chiral alcohols with retention of the configuration, electron-deficient phenols, as well as various natural alcohols. The usage of inexpensive copper catalyst, broad substrate scope, and neutral and open air conditions make this protocol very practical. 18O labeling experiments reveal that oxygenation occurs during this transformation. Preliminary mechanism studies indicate that two novel pathways are mainly involved in this process. (Chemical Equation Presented)
- Huang, Xiaoqiang,Li, Xinyao,Zou, Miancheng,Song, Song,Tang, Conghui,Yuan, Yizhi,Jiao, Ning
-
supporting information
p. 14858 - 14865
(2014/12/11)
-
- Cu-catalyzed esterification reaction via aerobic oxygenation and C-C bond cleavage: An approach to α-ketoesters
-
The Cu-catalyzed novel aerobic oxidative esterification reaction of 1,3-diones for the synthesis of α-ketoesters has been developed. This method combines C-C σ-bond cleavage, dioxygen activation and oxidative C-H bond functionalization, as well as provides a practical, neutral, and mild synthetic approach to α-ketoesters which are important units in many biologically active compounds and useful precursors in a variety of functional group transformations. A plausible radical process is proposed on the basis of mechanistic studies.
- Zhang, Chun,Feng, Peng,Jiao, Ning
-
supporting information
p. 15257 - 15262
(2013/11/06)
-