53226-42-9Relevant academic research and scientific papers
Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
supporting information, p. 5022 - 5037 (2021/05/04)
Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
UV-Light-Induced N-Acylation of Amines with α-Diketones
Xu, Zhihui,Yang, Tianbao,Tang, Niu,Ou, Yifeng,Yin, Shuang-Feng,Kambe, Nobuaki,Qiu, Renhua
supporting information, p. 5329 - 5333 (2021/07/21)
Herein, we develop a mild method for N-acylation of primary and secondary amines with α-diketones induced by ultraviolet (UV) light. Forty-six examples with various functional groups are explored at room temperature with irradiation by three 26 W UV lamps (350-380 nm). The yield reaches 97%. The gram scale experiment product yield is 76%. Moreover, this system can be applied to the synthesis of several amino acid derivatives. Mechanistic studies show that benzoin is generated in situ from benzil under UV irradiation.
Two-step continuous flow synthesis of amide via oxidative amidation of methylarene
Fang, Zheng,Guo, Kai,He, Wei,Liu, Chengkou,Shi, Tingting,Yang, Yuhang,Yang, Zhao,Zhang, Zhimin
supporting information, (2020/02/28)
A green and efficient method for the synthesis of amides has been developed through oxidative amidation between methylarenes with amines in a two-step continuous flow system. This method integrates methylarene oxidation and amide formation into a single operation which is usually accomplished separately. Oxidation with tert-butyl hydroperoxide (TBHP) as “green” oxidant, the synthesis of amides under mild reaction conditions in continuous flow system and the utilization of methylarenes as starting material make this methodology novel and environment friendly. The practical value of this method is highlighted through the synthesis of high-profile pharmaceutical agents, acetylprocainamide.
Electrophilic Activation of Amides for the Preparation of Polysubstituted Pyrimidines
Stopka, Tobias,Adler, Pauline,Hagn, Gerhard,Zhang, Haoqi,Tona, Veronica,Maulide, Nuno
supporting information, p. 194 - 202 (2019/01/04)
In this article we describe the straightforward synthesis of polysubstituted pyrimidines by electrophilic activation of secondary amides in the presence of alkynes. An unusual mechanistic detour leading to pyridine derivatives as products is also presente
An efficient transformation of methyl ethers and nitriles to amides catalyzed by Iron(III) perchlorate hydrate
Yin, Guibo,Yan, Bin,Chen, Junqing,Ji, Min
, p. 1355 - 1363 (2019/04/30)
An efficient and inexpensive synthesis of N-substituted amides from the reaction of nitriles with methyl ethers catalyzed by Fe(ClO4)3·H2O is described. Fe(ClO4)3·H2O is an economically efficient catalyst for the Ritter Reaction under solvent-free conditions. A range of methyl ethers (benzyl, sec-alkyl and tert-butyl ethers) were reacted with nitriles to provide the corresponding amides in high–excellent yields.
Nickel-Catalyzed Amide Bond Formation from Methyl Esters
Ben Halima, Taoufik,Masson-Makdissi, Jeanne,Newman, Stephen G.
supporting information, p. 12925 - 12929 (2018/09/14)
Despite being one of the most important and frequently run chemical reactions, the synthesis of amide bonds is accomplished primarily by wasteful methods that proceed by stoichiometric activation of one of the starting materials. We report a nickel-catalyzed procedure that can enable diverse amides to be synthesized from abundant methyl ester starting materials, producing only volatile alcohol as a stoichiometric waste product. In contrast to acid- and base-mediated amidations, the reaction is proposed to proceed by a neutral cross coupling-type mechanism, opening up new opportunities for direct, efficient, chemoselective synthesis.
FeCl2·4H2O catalyzed ritter reaction with nitriles and halohydrocarbons
Feng, Cheng-Liang,Yin, Gui-Bo,Yan, Bin,Chen, Jun-Qing,Ji, Min
, p. 345 - 353 (2019/02/12)
An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with various halohydrocarbons catalyzed by FeCl2·4H2O is described. FeCl2·4H2O economically efficiently catalyzed the Ritter reaction under solvent-free conditions. A range of halohydrocarbons (benzyl, tert-butyl and sec-alkyl halohydrocarbons) were coupled with nitriles to provide the corresponding amides in high to excellent yields.
Metal-Free C-N or C-C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides
Yu, Pei,Wang, Yuwei,Zeng, Zhigang,Chen, Yunfeng
, p. 14883 - 14891 (2019/11/11)
A novel metal-free oxidative-amidation strategy for the synthesis of α-ketothioamides and amides from α-azido ketones was developed. The C-H bond thionation of α-azido ketones with elemental sulfur could form α-ketothioacyl azide, which was then nucleophilically attacked by amines, causing the cleavage of the C-N bond to afford α-ketothioamides, while amides could be formed with the release of nitrogen gas and cyano anion in the presence of PhI(OAc)2 by selective C-C bond cleavage.
Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride
Zhang, Jin,Hou, Yanyan,Ma, Yangmin,Szostak, Michal
, p. 338 - 345 (2019/01/10)
A general Pd-catalyzed synthesis of amides by oxidative aminocarbonylation of arylsilanes under mild conditions was accomplished for the first time. The reaction is promoted by a commercially available copper(II) fluoride, which acts as a dual silane activator and mild oxidant, enabling highly efficient aminocarbonylation of versatile arylsilanes at atmospheric CO pressure. The reaction is tolerant of a wide range of arylsilanes and various sensitive halide functional groups as well as a broad scope of amines are compatible with this oxidative process using cheap CO. A significant aspect involves the increased efficiency by the catalyst system. The reaction represents a segue into the powerful Pd-catalyzed oxidative transformations of organosilanes.
Convenient synthesis of amides by Zn(ClO4)2·6H2O catalysed Ritter reaction with nitriles and halohydrocarbons
Feng, Chengliang,Yin, Guibo,Yan, Bin,Chen, Junqing,Ji, Min
supporting information, p. 383 - 386 (2018/08/21)
A convenient and high yielding procedure for the synthesis of amides by the Ritter reaction of nitriles and halohydrocarbons in the presence of Zn(ClO4)2·6H2O as a highly stable, effective and available catalyst is described.
