1310708-89-4

Upstream product

• 1722-12-9 2-chloropyrimidine 
• 83-34-1 3-Methylindole 

Downstream Products

• 10257-92-8 2-phenyl-3-methyl-1H-indole 
• 1310709-03-5 2-(4-methoxyphenyl)-3-methyl-1-(pyrimidin-2-yl)-1H-indole 
• 1414866-61-7 C₂₀H₁₈N₄O₂S 
• 1414866-79-7 C₁₆H₁₆N₂O₂S 
• 1427669-95-1 (3-methyl-1-(pyrimidin-2-yl)-1H-indol-2-yl)(phenyl)methanone 

Relevant academic research and scientific papers

Base-promoted SNAR reactions of fluoro- And chloroarenes as a route to N-aryl indoles and carbazoles

KOH/DMSO-promoted C-N bond formation via nucleophilic aromatic substitution (SNAr) between chloroarenes or fluoroarenes with indoles and carbazole under transition metal-free conditions affording the corresponding N-arylated indoles and carbazoles has been developed.

Rhodium-Catalyzed C?H Functionalization of N-(2-Pyrimidyl)indole with Internal Alkynes: Formation of Unexpected Products by Regulating the Amount of Silver Acetate

Herein we disclose an uncommon Rhodium(III)-catalyzed C2-selective functionalization of N-(2-Pyrimidyl)indole with internal alkynes. Excess amounts of silver acetate (5.0 equiv.) were found to be crucial for the efficient C2 naphthylation and C2 enol esterification of indoles. In sharp contrast, 2.0 equivalents of silver acetate resulted in the C?H alkenylation only. Control experiments were also carried out to briefly study the mechanism of this transformation. (Figure presented.).

Rhodium (III)-catalyzed regioselective direct C-2 alkenylation of indoles assisted by the removable N-(2-pyrimidyl) group

The C-2-alkenylindole unit is a key component of numerous natural products and pharmacophores. However, the intermolecular direct construction of the core structural motif remains challenging in organic synthesis. Here we report a new, efficient, and versatile methodology for the synthesis of C-2-alkenylindoles through rhodium (III)-catalyzed direct C-H functionalization of indoles with acrylates under air by employing a metal-directing group strategy. This strategy gives a rare selectivity for the alkenylation N-(2-pyrimidyl)indoles at the C-2 position and provides the functionalized C-2- alkenylindoles under mild conditions with broad substrate tolerance. An expansion of the methodology has also been demonstrated to, for example, the direct alkenylation of pyrrole and facile deprotection of the pyrimidyl group. All the results suggest that this methodology could be served as a highly attractive alternative for the direct construction of biologically important C-2-alkenylindoles.

CF2DSO2Na: An Effective Precursor Reagent for Deuteriodifluoromethylthiolation and Deuteriodifluoromethylation

Deuteriodifluoromethythio (SCF2D) and deuteriodifluoromethyl (CF2D) are important functional groups in pharmaceutical and agrochemical compounds, and the introduction of these functional groups remains a challenging. We herein report a robust reagent for deuteriodifluoromethylthiolation and deuteriodifluoromethylation. Its potentials were successfully showcased by deuteriodifluoromethylation and deuteriodifluoromethylthiolation of indoles with high-level deuterium incorporation. The reagent also has potential for deuteriodifluoromethylation and deuteriodifluoromethylthiolation of wide range of other natural or synthetic bioactive molecules.

Rhodium-Catalyzed Additive-Free C?H Ethoxycarbonylation of (Hetero)Arenes with Diethyl Dicarbonate as a CO Surrogate

A rhodium-catalyzed C(sp2)-H ethoxycarbonylation of indoles and arylpyridines using diethyl dicarbonate was developed. The catalytic process features an additive-free ethoxycarbonylation reaction, in which only ethanol and CO2 are produced as byproducts, providing a CO-free and operationally simple protocol. The introduced ethoxycarbonyl group is easily transformed into other ester and amide functionalities in a single step. Moreover, the reaction can be successfully applied on gram scale, and allows for the efficient synthesis of indole-2-carboxylic acid esters and isophthalates.

Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp2)-H Bonds Enabled by Cobalt Catalysis

We report a chelation-assisted C-H arylation of various indoles with sterically and electronically diverse (hetero)arylsilanes enabled by cost-effective Cp*-free cobalt catalysis. Key to the success of this strategy is the judicious choice of copper(II) fluoride as a bifunctional sliane activator and catalyst reoxidant. This methodology features a broad substrate scope and good functional group compatibility. The synthetic versatility of this protocol has been highlighted by the gram-scale synthesis and late-stage diversification of biologically active molecules.

The copper(ii)-catalyzed and oxidant-promoted regioselective C-2 difluoromethylation of indoles and pyrroles

A novel and efficient approach for the highly selective C-2 difluoromethylation of indole derivatives was developed by using sodium difluoromethylsulfinate (HCF2SO2Na) as the source of difluoromethyl groups and a Cu(ii) complex as the catalyst. Various substrates were well tolerated in this transformation and the desired products were obtained in moderate to good yields. Moreover, the late-stage C-2 difluoromethylation of bioactive molecules containing an indole ring was achieved in good yields. Generally, this reaction features excellent functional group compatibility, broad substrate scope and excellent C-2 selectivity. This journal is

Suzuki-Miyaura coupling of unstrained ketones via chelation-assisted C-C bond cleavage

Herein, we report that unstrained ketones can be efficiently employed as electrophiles in Suzuki-Miyaura reactions via catalytic activation of unstrained C-C bonds assist by an N-containing directing group. A wide range of aromatic ketones directly coupled with boronic ester with excellent functional group tolerance. This strategy provides an alternative and versatile approach to constructing biaryls from unstrained ketones.

Rhodium-catalyzed C-H functionalization with N-acylsaccharins

A rhodium-catalyzed C-H functionalization with activated amides by decarbonylation has been developed. Notably, this is the first C-H arylation employing N-acylsaccharins as coupling partners to give biaryls in good to excellent yields. The highlight of the work is the high tolerance of functional groups such as formyl, ester, and vinyl and the use of a removable directing group.

Manganese-catalyzed synthesis of monofluoroalkenes: Via C-H activation and C-F cleavage

The manganese-catalyzed α-fluoroalkenylation of arenes via C-H activation and C-F cleavage has been described. This protocol provides a very useful method for the synthesis of monofluoroalkenes with predominant unconventional E-isomer selectivity which complements the existing strategies for the access to these molecular architectures. In addition, the selectivity of β-defluorination in the catalytic cycle not only determines the configurations of the products but also obviates the use of external oxidants, providing a good example in the exploitation of manganese-catalyzed redox-neutral C-H transformations.