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C(sp2)-C(sp3) cross-coupling reactions have been intensively studied in recent years.1) The reactions allow the introduction of alkyl groups into aromatic rings. Among the reactions, the cross-coupling reactions of aryl halides with alkyl halides and redox-active aliphatic carboxylic acids, etc., are known as reductive cross-electrophile couplings (CEC). TCI has five ligands for reductive cross-electrophile couplings (Product No. P3015, D6070, P2176, C3801, C3803). These ligands can be used in reductive cross electrophile couplings with nickel catalysts and metal powders as reducing agents. Bipyridyl ligands have been known to catalyze this reaction, but the ligands bearing carboxamidine group gives better results with some substrate combinations.2) In general, there are not as many options for nitrogen-donor ligands compared to phosphorus ligands. TCI has five types of carboximidamide-containing ligands with different properties and structures, which are useful for screening catalytic systems to match the desired reaction substrates.
![4,4'-Di-tert-Butyl-N-cyano[2,2'-bipyridine]-6-carboximidamide](https://www.tcichemicals.com/assets/cms-images/ligands_for_reductive_cross-electrophile_coupling_C3803.png)
Reductive cross-electrophile coupling can utilize alkyl halides, alkyl carboxylic acids, and alkyl amines as coupling partners. Conventional cross-coupling reactions mostly utilize organometallic reagents such as Grignard reagents and organoboron compounds. However, the alkyl group-containing coupling partners available for reductive cross electrophile coupling offer many advantages over organometallic reagents in terms of commercial availability, diversity, price, storage stability, and ease of handling.
Recent drug discovery chemistry favors sp3 carbon-rich compound design.3) The C(sp2)-C(sp3) cross-coupling reactions can be used to efficiently synthesize such compounds. In materials science, this reaction can be used to improve solubility by introducing long-chain alkyl groups to the aromatic rings that form the parent nucleus of functional compounds. We also have a large selection of related aliphatic building blocks, transition metal catalysts, reducing agents, bases, additives, and other synthetic reagents.
Products
- P3015
- Pyridine-2,6-dicarboximidamide Dihydrochloride (= PyBCam·HCl)
- D6070
- N2,N6-Dicyanopyridine-2,6-bis(carboximidamide) (= PyBCamCN)
- P2176
- Pyridine-2-carboximidamide Hydrochloride (= PyCam·HCl)
- C3801
- N'-Cyano-2-pyridinecarboximidamide (= PyCamCN)
- C3803
- 4,4'-Di-tert-Butyl-N-cyano[2,2'-bipyridine]-6-carboximidamide (= tBuBpyCamCN)
Applications
Cross coupling of alkyl halides and aryl halides 4)
Cross coupling of alkyl carboxylic acids and aryl halides 5)
Cross coupling of alkyl amines and aryl halides 6)
References
- 1) Expanding the Medicinal Chemist Toolbox: Comparing Seven C(sp2)−C(sp3) Cross-Coupling Methods by Library Synthesis
- 2) New Ligands for Nickel Catalysis from Diverse Pharmaceutical Heterocycle Libraries
- 3) Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success
- 4) Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling
- 5) Control of Redox-Active Ester Reactivity Enables a General Cross-Electrophile Approach to Access Arylated Strained Rings
- 6) Nickel-Catalyzed Electrochemical Reductive Cross-Electrophile Coupling of Alkylpyridinium Salts and Aryl Halides
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