tert-Butoxy-bis(dimethylamino)methane CAS:5815-08-7(Bredereck’s reagent) is a useful reagent for α-methylation, α-methylenation, and α-amination of several carbonyl systems or compounds with an active CH group.
Compared to the conventional methods to insert a methyl, methylene or amine groups at the position α to a carbonyl group, Bredereck’s reagent has the advantage of generating a strong basic alkoxide (t-BuO-) in situ and the corresponding iminium ion by thermal decomposition. After the Mannich reaction between the carbonyl substrate and the iminium ion formed in situ, β-elimination of dimethylamine from the adduct in the final step affords the condensation product which can be transformed into various types of compounds as shown below. These factors combine to make Bredereck’s reagent the reagent of choice for α-methylation, α-methylenation, and α-amination of carbonyl compounds.
Bredereck’s reagent CAS:5815-08-7 has been manufacturing and supplying in commercial size over 10 years from UCHEM, who commercialized it in concentration at 90% in DMF with competitive price and varied package size.
The 2,2'-bipyridine ligand has been extensively used as a metal chelating ligand due to its robust redox stability and ease of functionalization. In contrast to other ligands, such as catechol, which is dianionic, and derivatives of the acetylacetonate ion, which are monoanionic, 2,2'-bipyridine is a neutral ligand. It thus forms charged complexes with metal cations, and this property has been exploited in the design and synthesis of metal-bipyridine complexes.
Ligands containing two or more 2,2'-bipyridine units can in principle be used as bridges to interconnect metal centers in a well-defined spatial arrangement. The uses of such ligands as precursors for helical assembly, chiral molecular recognition, luminescent devices, and other applications in photonics and optoelectronics and electrochemistry have been studying extensively.
Chiral C2-symmetric vicinal diamines have emerged as powerful tools for the synthesis of enantiomerically pure compounds and are now commonly used as chiral auxiliaries or ligands for a wide array of asymmetric chemical transformations, with efficiencies comparable to those obtained with the closely related 1,2-diols. (1S,2S)- 1,2-Diaminocyclohexane (also named (IS,2S)-1,2-cyclohexanediamine), together with its (1R, 2R) enantiomer, allows excellent levels of asymmetric induction in many reactions, for which it has become the ligand of choice. Its applications in asymmetric synthesis and catalysis often involves the preparation of various N,N'-substituted derivatives.
Chirality is a geometric property of some molecules and ions. A chiral molecule/ion is non-superimposable on its mirror image. The presence of an asymmetric carbon center is one of several structural features that induce chirality in organic and inorganic molecules. The term chirality is derived from the Greek word for hand.
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