76426-76-1Relevant academic research and scientific papers
Chemical Upcycling of Waste Poly(bisphenol A carbonate) to 1,4,2-Dioxazol-5-ones and One-Pot C?H Amidation
Jung, Hyun Jin,Park, Sora,Lee, Hyun Sub,Shin, Hyun Gyu,Yoo, Yeji,Baral, Ek Raj,Lee, Jun Hee,Kwak, Jaesung,Kim, Jeung Gon
, p. 4301 - 4306 (2021/07/09)
Chemical upcycling of poly(bisphenol A carbonate) (PC) was achieved in this study with hydroxamic acid nucleophiles, giving rise to synthetically valuable 1,4,2-dioxazol-5-ones and bisphenol A. Using 1,5,7-triazabicyclo[4.4.0]-dec-5-ene (TBD), non-green carbodiimidazole or phosgene carbonylation agents used in conventional dioxazolone synthesis were successfully replaced with PC, and environmentally harmful bisphenol A was simultaneously recovered. Assorted hydroxamic acids exhibited good-to-excellent efficiencies and green chemical features, promising broad synthetic application scope. In addition, a green aryl amide synthesis process was developed, involving one-pot depolymerization from polycarbonate to dioxazolone followed by rhodium-catalyzed C?H amidation, including gram-scale examples with used compact discs.
Ortho–C–H amidations enabled by a recyclable manganese-ionic liquid catalytic system
Kong, Xianqiang,Xu, Bo
, (2019/12/27)
We described an environmentally benign, recyclable base metal catalyst system (MnBr(CO)5/[Hmim]OAc) for ortho–C–H amidation. The readily available dioxazolones was used as the amidation agents. A broad substrate scope and high functional group
Co(III)-Catalyzed C-H Amidation of Nitrogen-Containing Heterocycles with Dioxazolones under Mild Conditions
Dhiman, Ankit Kumar,Thakur, Ankita,Kumar, Inder,Kumar, Rakesh,Sharma, Upendra
, p. 9244 - 9254 (2020/08/14)
A cobalt(III)-catalyzed C-8 selective C-H amidation of quinoline N-oxide using dioxazolone as an amidating reagent under mild conditions is disclosed. The reaction proceeds efficiently with excellent functional group compatibility. The utility of the current method is demonstrated by gram scale synthesis of C-8 amide quinoline N-oxide and by converting this amidated product into functionalized quinolines. Furthermore, the developed catalytic method is also applicable for C-7 amidation of N-pyrimidylindolines and ortho-amidation of benzamides.
Dibenzothiophenesulfilimines: A Convenient Approach to Intermolecular Rhodium-Catalysed C?H Amidation
Antoni, Patrick W.,Mackenroth, Alexandra V.,Mulks, Florian F.,Rudolph, Matthias,Helmchen, Günter,Hashmi, A. Stephen K.
supporting information, p. 8235 - 8238 (2020/06/17)
A sulfilimine-based Group 9 transition-metal-catalysed C?H amidation procedure is reported. Dibenzothiophene-based sulfilimines were shown to constitute a class of novel amidation reagents which enable the transfer of a wide range of N-sulfonyl and N-acyl
Rhodium-Catalyzed C?H Activation Enabled by an Indium Metalloligand
Yamada, Ryosuke,Iwasawa, Nobuharu,Takaya, Jun
supporting information, p. 17251 - 17254 (2019/11/13)
Rhodium complexes with an indium metalloligand were successfully synthesized by utilizing a pyridine-tethered cyclopentadienyl ligand as a support for an In?Rh bond. The indium metalloligand dramatically changes the electronic and redox properties of the
N-Methoxyamide: An Alternative Amidation Reagent in the Rhodium(III)-Catalyzed C-H Activation
Zhou, Chao,Zhao, Junqi,Guo, Weicong,Jiang, Jijun,Wang, Jun
supporting information, p. 9315 - 9319 (2019/11/28)
In the field of transition-metal-catalyzed C-H activation, N-methoxyamides are widely used as C-H activation substrate. Unexpectedly, in this work N-methoxyamides were found to work as efficient amidation reagents in the rhodium(III)-catalyzed C-H activation with boric acid as a cocatalyst. This reaction features broad substrate scope and good yields.
Rh(III)-Catalyzed C-H Amidation of Arenes with N-Methoxyamide as an Amidating Reagent
Ju, Guodong,Li, Guobao,Qian, Guanwen,Zhang, Jingyu,Zhao, Yingsheng
supporting information, p. 7333 - 7336 (2019/10/08)
The Rh(III)-catalyzed amidation of C(sp2)-H bonds has been reported by employing the N-methoxyamide as a novel amino source. An excellent level of functional group tolerance can be achieved when N-methoxyamide derivatives are used as the amidating reagents. Importantly, several known bioactive compounds such as Aminalon, Pregabalin, Gabapentin, and Probenecid can be transformed to effective amidating reagents, as a way to facilitate the development of new bioactive molecules.
Lewis Acid/Br?nsted Acid Controlled Pd(II)-Catalyzed Chemodivergent Functionalization of C(sp2)-H Bonds with N-(Arylthio)i(a)mides
Chaitanya, Manthena,Anbarasan, Pazhamalai
supporting information, p. 3362 - 3366 (2018/06/11)
An efficient and chemodivergent palladium-catalyzed thiolation (C-S) and imidation (C-N) of directing group-assisted C-H bonds have been accomplished employing N-(arylthio)imides in combination with either Br?nsted acid or Lewis acid, respectively. Notable features of the developed methodologies include excellent diversity, high functional group tolerance, wide substrate scope, and use of a single N-S reagent. Importantly, the developed hypothesis was also successfully extended to the amidation of C-H bonds. A plausible mechanistic pathway was proposed based on the preliminary mechanistic study.
Efficient preparation of o-amidated aryl heterocyclic derivatives by transition metal catalyzed C-H coupling
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Paragraph 0016; 0017, (2018/10/24)
The invention relates to a novel green synthesis method for preparing o-amidated aryl heterocyclic derivatives from an N1,N3-disubstituted imidazole ionic liquid as a solvent and dioxazolone compoundsas an amide source by transition metal catalyzed C-H coupling reaction. Compared with the traditional technology, the method is safer, simpler, more efficient and more environmentally friendly; a functional group has good tolerance and high yield; the solvent and a catalyst can be recycled, and the cost is greatly reduced; the by-product is merely carbon dioxide, a large amount of waste is avoided, and the atomic utilization rate is increased; pre-activation of a substrate is not needed, the reaction conditions are mild, and the operation difficulty is reduced. An o-amidated aryl heterocyclicderivative molecular library can be obtained efficiently and quickly, natural compounds can be modified later, and accordingly, new drug candidate molecules are synthesized.
[Cp*RhIII]/Ionic Liquid as a Highly Efficient and Recyclable Catalytic Medium for C?H Amidation
Ma, Qiang,Yu, Xinling,Lai, Ruizhi,Lv, Songyang,Dai, Weiyang,Zhang, Chen,Wang, Xiaolong,Wang, Qiantao,Wu, Yong
, p. 3672 - 3678 (2018/09/29)
A [Cp*RhIII]-catalyzed direct C?H amidation is carried out in ionic liquid. Both C(sp2)?H bonds of (hetero)arenes and alkenes and unactivated C(sp3)?H bonds can be easily amidated with high functional-group tolerance and excellent yields under these conditions. Notably, using [Cp*RhIII]/[BMIM]BF4 (BMIM=1-butyl-3-methylimidazolium) as the green and recyclable medium is environmentally benign, in light of characteristics such as the reusability of the expensive rhodium catalyst, avoidance of highly toxic organic solvents, and mild reaction conditions, as well as a short reaction time.
