14213-19-5

Upstream product

• 506-68-3 bromocyane 
• 371-40-4 4-fluoroaniline 
• 459-05-2 (4-fluoro-phenyl)-thiourea 
• 1194-02-1 4-fluorobenzonitrile 
• 459-57-4 4-fluorobenzaldehyde 
• 459-23-4 4-fluorobenzaldoxime 
• 22179-78-8 4-fluoro-benzamidoxime 
• 1544-68-9 4-fluorophenyl isothiocyanate 
• 420-04-2 CYANAMID 
• 352-34-1 4-fluoro-1-iodobenzene 

Downstream Products

• 459-05-2 (4-fluoro-phenyl)-thiourea 
• 18201-87-1 2-[(4-fluorophenyl)amino]benzonitrile 
• 30895-14-8 1-(4-fluorophenyl)-1H-tetrazol-5-amine 
• 1046786-81-5 N-(4-fluorolphenyl)-2-oxo-2-phenylacetamide 
• 1345028-80-9 C₁₁H₁₁FN₂O₂ 
• 1414382-25-4 1-(4-fluorophenyl)-5-methyl thiohydantoin 

Relevant academic research and scientific papers

Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions

The iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology. All the reactions are rapid, facile, and accomplished at room temperature. A variety of substrates readily underwent the optimized reaction conditions to provide their respective target products in good to excellent yields. Furthermore, we have confirmed that no other by-products could be identified during our experimental reaction process. Graphical abstract: Iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology.[Figure not available: see fulltext.].

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.

CF3SO2Na as a Bifunctional Reagent: Electrochemical Trifluoromethylation of Alkenes Accompanied by SO2 Insertion to Access Trifluoromethylated Cyclic N-Sulfonylimines

An unprecedented electrochemical trifluoromethylation/SO2 insertion/cyclization process has been achieved in an undivided cell in an atom-economic fashion. The protocol relies on tandem cyclization of N-cyanamide alkenes by using Langlois’ reagent as a source of both CF3 and SO2 under direct anodically oxidative conditions, in which two C?C bonds, two C?X bonds (N?S and S?C), and two rings were formed in a single operation. This transformation enabled efficient construction of various trifluoromethylated cyclic N-sulfonylimines from readily accessible materials.

A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement

A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.

One-pot three-component tandem reaction: Synthesis of aryl/alkyl cyanamides libraries and their further conversion into tetrazole derivatives

We have developed methodology for the synthesis of aryl/alkyl cyanamides from amines in one-pot four steps reaction using cheap, readily available and air stable copper source as catalyst under mild reaction conditions. We have also studied the application of cyanamides. In this connection, we could construct aryl tetrazolamine from cyanamides using click reaction.

Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles

[Figure not available: see fulltext.] The synthesis of cyanamides and tetrazoles from isothiocyanates through tandem reaction using cobalt catalyst has been demonstrated. In the case of tetrazole preparation, the reaction involved addition/desulfurization/nucleophilic addition/electrocyclization, whereas aromatic cyanamides were constructed from isothiocyanates through addition/desulfurization. Cheap cobalt sulfate was used for the synthesis of various cyanamides and tetrazoles. In addition, cobalt catalyst was found to be desulfurization reagent that has not been previously reported. The final products have been obtained from starting precursors in good to high yield.

The synthesis of aryl cyanamides through C-N cross-coupling

The methodology for the preparation of aromatic cyanamides has been demonstrated. The present method involves consecutive desulphurization/C-N cross-coupling reaction. Cheap, readily available and air stable cobalt catalyst has been used for this methodology. In addition, the substrate scope has been explored.

The synthesis of arylcyanamides: A copper-catalyzed consecutive desulfurization and C-N cross-coupling strategy

A one pot highly efficient and simple protocol for the construction of aromatic cyanamides from thiourea via desulphurization/C-N cross coupling using a cheap, readily available and air stable copper source as a catalyst has been described. Various iodobenzenes could give their respective C-N cross-coupled products in good to excellent yields under optimized reaction conditions. Further, the substrate scope has been explored.

Synthesis of cyanamides from isoselenocyanates promoted by recyclable ionic liquid-supported (diacetoxyiodo)benzene

One-pot synthesis of cyanamides from isoselenocyanates through deselenisation promoted by ionic liquid-supported hypervalent iodine(III) reagent 1-(4-diacetoxyiodobenzyl)-3-methylimidazolium tetrafluoroborate [dibmim BF4 was developed. This approach provided a simple, mild and environmentally benign way to construct cyanamides in good yields. Moreover, powder Se and dibmim + BF4 could be easily recycled. It was the first example of [dibmim] + [BF4- to be used as a deselenising agent.

Aminocyanation by the addition of N-CN bonds to arynes: Chemoselective synthesis of 1,2-bifunctional aminobenzonitriles

An efficient aminocyanation by the direct addition of aryl cyanamides to arynes is described, enabling incorporation of highly useful amino and cyano groups synchronously via cleavage of inert N-CN bonds, affording synthetically useful 1,2-bifunctional aminobenzonitriles. The postsynthetic functionalization of the aminocyanation products allows diverse formation of synthetically important derivatives such as drug molecule Ponstan and fused heterocycles.