23518-17-4Relevant articles and documents
Efficient and mild oxidative nuclear thiocyanation of activated aromatic compounds using ammonium thiocyanate and diacetoxyiodobenzene
Karade,Tiwari,Shirodkar,Dhoot
, p. 1197 - 1201 (2005)
A mild and general method for the nuclear thiocyanation of electron rich arenes has been developed by the reaction of NH4SCN with diacetoxyiodobenzene as the oxidant. Copyright Taylor & Francis, Inc.
Regioselective thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and oxone
Wu, Guaili,Liu, Qiang,Shen, Yinglin,Wu, Wentao,Wu, Longmin
, p. 5831 - 5834 (2005)
An efficient and regioselective approach for the thiocyanation of indoles, pyrrole, aromatic amino compounds, and 2-methoxycarbazole has been developed using ammonium thiocyanate as a thiocyanation reagent and oxone as an oxidant.
A clay-mediated eco-friendly thiocyanation of indoles and carbazoles
Chakrabarty, Manas,Sarkar, Sandipan
, p. 8131 - 8133 (2003)
Indoles 1a-f and carbazoles 3a-c on treatment with ammonium thiocyanate on montmorillonite K10 clay at 80°C furnished the corresponding 3-thiocyanato derivatives 2a-f and 4a-c in good to high yields. Skatole 5 furnished the dimeric oxindole 6, which resulted from autoxidation.
Two-step synthesized sulfonic acid functionalized imidazolium thiocyanate solid acid catalyst for thiocyanation of various electron rich arenes by metal-free method in water
Naserifar, Zahra,Ramazani, Ali,Rezayati, Sobhan
, (2022/03/27)
An eco-friendly, highly efficient, and novel sulfonic acid functionalized imidazolium thiocyanate (Imidazole-SO3H)/SCN and sulfonic acid functionalized imidazolium chloride (Imidazole-SO3H)/Cl solid acid catalyst were successfully synthesized. The structure of catalyst was characterized by various analyses such as FT-IR, 1H NMR and 13C NMR spectroscopy. The thiocyanation reaction of various electron rich arenes such as anilines, indoles, phenols, and other aromatic compounds were selected to show the catalytic performance and efficiency of the as-prepared solid acid catalyst, and excellent yields of the corresponding aryl and heteroaryl thiocyanates derivatives were obtained under metal-free and green conditions in water. In addition, one of the important features of current method is when the thiocyanation reaction is carried out with (Imidazole-SO3H)/SCN, this reagent has a dual role in the reaction, both as thiocyanation agent and as acidic group. On the other hand, (Imidazole-SO3H)/Cl as a catalyst plays just as acidic group in reaction. The current procedure offers advantages such as metal-free and green conditions, simple procedure, the use of a commercially available reagent, simple reaction work-up, ease of separation using simple filtration, and suitable performance in the reusability of the catalyst.
Visible-light-promoted thiocyanation of sp2C-H bonds over heterogeneous graphitic carbon nitrides
Chen, Wei,Li, Tingzhen,Peng, Xinwen
supporting information, p. 14058 - 14062 (2021/08/16)
Mesoporous graphitic carbon nitride (mpg-C3N4) has been developed as a metal-free heterogeneous photocatalyst for thiocyanation transformations. The reaction proceeds efficiently by utilizing air as a green oxidant under mild reaction conditions, which affords SCN-containing compounds in moderate to excellent yields. Meanwhile, the practicality of this protocol is further demonstrated by the reusability of the mpg-C3N4photocatalyst and the scaled-up reaction. Furthermore, detailed mechanistic studies clearly demonstrate the role of oxygen.
Screening metal-free photocatalysts from isomorphic covalent organic frameworks for the C-3 functionalization of indoles
Chen, Xiong,Feng, Xiao,Han, Songjie,Li, Chunzhi,Li, He,Li, Ziping,Liu, Xiaoming,Shao, Pengpeng,Xia, Hong
supporting information, p. 8706 - 8715 (2020/05/16)
The visible-light-driven organic transformation using two-dimensional covalent organic frameworks (2D-COFs) as metal-free heterogeneous photocatalysts is a green and sustainable approach, and it has gained a surge of interest by virtue of the photosensitizer's high crystallinity, abundant porosity, outstanding stability, excellent light-harvesting ability and tunable structure. However, the guiding principle for designing, constructing and selecting COF-based photocatalysts has not been put forward so far. Herein, we contribute a fascinating strategy to guide the acquisition of excellent framework photocatalysts, which is to screen them from a series of isomorphic COFs. As a proof of concept, three new isomorphic pyrene-based 2D-COFs (COF-JLU23, COF-JLU24 and COF-JLU25) with variable linkers were successfully synthesized. In addition to having similar crystallinity and porosity with the same pore size and shape, their absorption, emission, bandgap, energy level, transient photocurrent response and photocatalytic activity could be easily adjustedviaconfiguring different linkers in frameworks. Indeed, COF-JLU24 with electron donor-acceptor characteristics exhibited the best photocatalytic activity among the three isomorphic COFs for C-3 functionalization reactions of indoles, even better than that of the metal-free photocatalyst g-C3N4. More importantly, the screened COF-JLU24 as a metal-free photocatalyst still displayed extensive substrate adaptability and excellent recyclability. We anticipate that this strategy will become a robust rule of thumb for fast access to COF-based photocatalysts. In addition, we still highlight that the present study broadens the applied frontier of COF-based photocatalysts.
