212313-35-4Relevant academic research and scientific papers
Selective C(sp2)-H Amination Catalyzed by High-Valent Cobalt(III)/(IV)-bpy Complex Immobilized on Silica Nanoparticles
Budnikova, Yulia,Bochkova, Olga,Khrizanforov, Mikhail,Nizameev, Irek,Kholin, Kirill,Gryaznova, Tatyana,Laskin, Artem,Dudkina, Yulia,Strekalova, Sofia,Fedorenko, Svetlana,Kononov, Aleksandr,Mustafina, Asia
, p. 5615 - 5624 (2019)
High-valent cobaltIV-bpy complex stabilized in silica matrix was detected as catalytically active form and intermediate in cobalt-mediated oxidative C?H/NH cross-coupling reaction. These CoIV species prepared by electrooxidation of CoIII(bpy)3-doped silica nanoparticles (SNs) at relatively low anodic potentials have demonstrated high catalytic activity. Both size and architecture of the SNs are highlighted as the factors beyond the complex structure affecting its oxidation potential and catalytic efficiency. The factors have been optimized for the catalyst with high efficiency, easy separation and reusability for 7 times at least. The optimal nanocatalyst (1 mol%) provides 100 % conversion of reactants in a single step of ligand-directed coupling of H2NTs with arenes under electrochemical regeneration conditions. The results emphasize both synthetic route for efficient embedding of CoIII(bpy)3 into silica support and the electrochemical generation of CoIV complexes as a facile route for developing the efficient nanocatalyst of oxidative functionalization. The observed reactivity has the potential in development of Co-catalyzed coupling reactions.
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.
, 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
Manganese-Catalyzed C?H Amidation of Heteroarenes in Water
Kong, Xianqiang,Lin, Long,Xu, Bo
, p. 2801 - 2805 (2018/08/17)
We have developed an efficient manganese-catalyzed amidation of various heteroarenes via C?H bond activation using readily available sulfonyl azides. The key step is heteroarene directed electrophilic aromatic metalation using MnBr(CO)5 as catalyst. This method offers excellent chemical yields and regioselectivity with good functional group tolerance. This base metal catalyzed reaction proceeds efficiently using water as the only solvent and nitrogen is the only byproduct. (Figure presented.).
RuHCl(CO)(PPh3)3-Catalyzed Direct Amidation of Arene C-H Bond with Azides
Xiao, Xinsheng,Jia, Guokai,Liu, Fang,Ou, Guangchuan,Xie, Ying
supporting information, p. 13811 - 13820 (2018/11/23)
We first report the direct ortho C-H amidation of arenes with azides by using a novel and inexpensive RuHCl(CO)(PPh3)3 catalyst. The reaction proceeds efficiently in high yield over a broad range of substrates without requirement of any additional silver salt or additive.
Chelation-Assisted Rhodium-Catalyzed Direct Amidation with Amidobenziodoxolones: C(sp2)-H, C(sp3)-H, and Late-Stage Functionalizations
Hu, Xu-Hong,Yang, Xiao-Fei,Loh, Teck-Peng
, p. 5930 - 5934 (2016/09/09)
Air-stable and convenient amidobenziodoxolones as an amidating reagent were disclosed to enable direct amidation on a wide range of C(sp2)-H bonds of (hetero)arenes and alkenes, as well as unactivated C(sp3)-H bonds under RhIII catalysis. The approach to access 49 examples of structurally diverse amides is featured by mild conditions, complete chemoselectivity and regioselectivity, broad substrate scope (not limited to strongly heterocyclic coordinating groups), and tolerance of valuable functional substituents, such as unprotected amine and hydroxyl groups. The synthetic applicability of this protocol is also demonstrated by late-stage functionalization of biologically important scaffolds.
Cobalt(III)-catalyzed C-H amidation of arenes using acetoxycarbamates as convenient amino sources under mild conditions
Patel, Pitambar,Chang, Sukbok
, p. 853 - 858 (2015/02/19)
The Co(III)-catalyzed direct C-H amidation of arenes has been developed using O-acylcarbamates as a convenient amino source. This reaction proceeded in high efficiency under external oxidant-free conditions with a broad range of arene substrates, includin
Ruthenium-catalyzed direct C-H amidation of arenes: A mechanistic study
Zhang, Lu,Li, Lian-Hua,Wang, Yu-Qi,Yang, Yan-Fang,Liu, Xue-Yuan,Liang, Yong-Min
supporting information, p. 1905 - 1908 (2014/05/20)
We report mechanistic studies of C-H activitation/amidation reactions using azides as the amino source catalyzed by [RuCl2(p-cymene)] 2. We have achieved two intermediates in the catalytic cycle (C 5H4NC6H4)Ru(p-cymene)Cl and (C 5H4NC6H4)NArRu(p-cymene)Cl (Ar = NO2C6H4SO2). Furthermore, the process from (C5H4NC6H4)Ru(p-cymene) Cl to (C5H4NC6H4)NArRu(p-cymene)Cl was monitored by 19F NMR and a ruthenium-imido species was proposed to explain the formation of the azacyclopropane analogue.
Copper-catalyzed C(sp2)-H amidation with azides as amino sources
Peng, Jiangling,Xie, Zeqiang,Chen, Ming,Wang, Jian,Zhu, Qiang
supporting information, p. 4702 - 4705 (2015/04/27)
A copper-catalyzed C-H amidation process, with azides as amino sources under oxidant-free conditions, has been developed. When N-heterocycles were employed as directing groups, sulfonylazide and benzoylazide could be used as amidating reagents to provide corresponding N-arylamides. When amidines or imine were used, tandem C-N/N-N bond formation occurred to afford indazole derivatives in one pot.
