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Upstream product

• 1380503-24-1 5-fluoro-1-(pyrimidin-2-yl)-1H-indole 
• 2996-92-1 phenyl trimethylsiloxane 
• 65-85-0 benzoic acid 
• 81-07-2 saccharin 
• 28284-05-1 N-benzoylisatin 
• 91-56-5 indole-2,3-dione 
• 98-80-6 phenylboronic acid 
• 37952-93-5 N-benzoyl saccharin 
• 399-52-0 5-fluoro-1H-indole 

Relevant academic research and scientific papers

Cobalt-catalyzed intramolecular decarbonylative coupling of acylindoles and diarylketones through the cleavage of C-C bonds

We report here cobalt-N-heterocyclic carbene catalytic systems for the intramolecular decarbonylative coupling through the chelation-assisted C-C bond cleavage of acylindoles and diarylketones. The reaction tolerates a wide range of functional groups such as alkyl, aryl, and heteroaryl groups, giving the decarbonylative products in moderate to excellent yields. This transformation involves the cleavage of two C-C bonds and formation of a new C-C bond without the use of noble metals, thus reinforcing the potential application of decarbonylation as an effective tool for C-C bond formation. This journal is

Selective C?N Bond Cleavage of N-Acylisatins: Towards High Performance Acylation/Arylation/Transamination Reagents

New multipurpose arylation/acylation/transamination reagents, N-acylisatins, have been developed by selective ‘inside-outside’ C?N bond cleavage under different catalytic conditions. As activated amides, N-acylisatins undergo Rh-catalyzed C?H arylation and Pd-catalyzed acylation by cleavage outside the C?N bond, and the desired biaryls and diaryl ketones were obtained in good to excellent yields. Generally, the combination of N-acylisatins with amines leads to a ring-opening reaction and formation of transamination products in a predictable manner through inside C?N bond cleavage. Interestingly, treatment of N-acylisatins with amines lead to unexpected outer-ring transamination products when CsF is added, which shows that CsF can favor the outside C?N bond cleavage path. Notably, this work presents a new strategy for multiple chemical transformations of a single amide to achieve various products by selective C?N bond cleavage. (Figure presented.).

Directed Decarbonylation of Unstrained Aryl Ketones via Nickel-Catalyzed C - C Bond Cleavage

The nickel-catalyzed decarbonylation of unstrained diaryl ketones has been developed. The reaction is catalyzed by a combination of Ni(cod)2 and an electron-rich N-heterocyclic carbene ligand. High functional group tolerance and excellent yields (up to 98%) are observed. This strategy provides an alternative and versatile approach to construct biaryls using an inexpensive nickel catalyst.

Ruthenium(II)-Catalyzed Direct C-H Arylation of Indoles with Arylsilanes in Water

The ruthenium(II)-catalyzed, heteroatom-directed C-H arylation of indoles with arylsilanes in water has been developed. The method represents the first example of a ruthenium(II)-catalyzed oxidative C-H arylation in water/aqueous media as a sustainable solvent for C-H functionalization. The reaction enables the synthesis of a wide range of indoles with exquisite selectivity for arylation at the C-2 position. Preliminary mechanistic studies indicate reversibility of the C-H ruthenation step under the developed reaction conditions.

Cobalt(II)-Catalyzed Oxidative C-H Arylation of Indoles and Boronic Acids

Co(II)-catalyzed C-H C2 selective arylation of indoles with boronic acids through monodentate chelation assistance has been achieved for the first time. The unique features of this methodology include mild reaction conditions, highly C2 regioselectivity, and employment of a Grignard reagent-free catalytic system. A wide range of substrates, including unreactive arenes, are well tolerated, which enables the construction of the coupling products efficiently. This new strategy provides an alternative and versatile approach to construct biaryls using inexpensive cobalt catalyst.

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.

Rhodium-catalyzed decarbonylative direct C2-arylation of indoles with aryl carboxylic acids

A RhI-catalyzed direct C2-arylation of indoles with diversely substituted aryl carboxylic acids has been developed using 2-pyrimidyl group as an easily installable and readily removable N-directing group. The reaction proceeded smoothly without the need for any external oxidants under relatively mild conditions to produce the C2-arylated indoles in high yields with excellent regioselectivity. A range of functional groups in both coupling partners were tolerated regardless of their electronic properties and positions. With the assistance of the 2-pyrimidyl group, these C2-functionalized products could further undergo C7-arylation to give the C7-aryl indole products. Mechanistic evidence supports that the reaction involves a decarbonylation step, and the carboxylic acids could be activated in situ by treatment with (tBuCO)2O to generate the active anhydrides.

Mild Rh(III)-catalyzed direct C-H bond arylation of (hetero)arenes with arylsilanes in aqueous media

An efficient rhodium(III)-catalyzed C-H bond activation and further direct arylation of (hetero)arenes with organosilanes in aqueous media was developed. This reaction shows good substrate scope and excellent functional group compatibility and gives the products in good yields with excellent regioselectivity.