34171-46-5Relevant articles and documents
Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters
Huang, Changyu,Li, Jinpeng,Wang, Jiaquan,Zheng, Qingshu,Li, Zhenhua,Tu, Tao
, p. 66 - 71 (2020/11/18)
The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]
Solar and visible-light active nano Ni/g-C3N4photocatalyst for carbon monoxide (CO) and ligand-free carbonylation reactions
Hosseini-Sarvari, Mona,Akrami, Zahra
, p. 956 - 969 (2021/02/26)
In this study, we investigate the amino and alkoxycarbonylation reaction between various substituted aryl halides, benzyl iodides, and iodocyclohexane with different types of amines and alcohols in the absence of carbon monoxide gas and ligands. Similar reactions are carried out at high temperatures, in the presence of appropriate ligands, stoichiometric amounts of bases, and gaseous carbon monoxide, which endanger the health of organic chemists. We present a novel method that does not utilize ligands, bases, gaseous CO, and special conditions. This procedure is a redox reaction carried out by new economic nano Ni/g-C3N4at room temperature and under visible light. Mo(CO)6was used toin situgenerate CO, to resolve the problems caused by the use of CO gas. This protocol has the ability to be used on a gram scale by using a continuous flow reactor.
Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles
Mahajani, Nivedita S.,Meador, Rowan I. L.,Smith, Tomas J.,Canarelli, Sarah E.,Adhikari, Arijit A.,Shah, Jigisha P.,Russo, Christopher M.,Wallach, Daniel R.,Howard, Kyle T.,Millimaci, Alexandra M.,Chisholm, John D.
, p. 7871 - 7882 (2019/06/27)
Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Br?nsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.
