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*N*-Boryl Pyridyl Anion Chemistry.

Pyridine is a crucial heterocyclic compound in organic chemistry. Typically, the pyridine motif behaves as an N-nucleophile and an electron-deficient aromatic ring. Transforming the pyridine ring into an electron-rich system that exhibits reactivity …

4-Pyridyl Perfluoroalkyl Sulfide as a Practical Nucleophilic Perfluoroalkylation Reagent.

The incorporation of perfluoroalkyl groups into molecules leads to unique properties, and perfluoroalkylation reagents play a vital role in facilitating this process. Although various types of perfluoroalkylation reagents have been developed, the …

Photoinduced Radical Borylation of Alkyl Chlorides.

The traditional method for the preparation of alkylboronic esters involves transition metal catalysis or transition metal-free methods relying on single electron transfer. Each method relies on the suitable choice of catalyst or electron transfer …

Modular Photoredox System with Extreme Reduction Potentials Based on Pyridine Catalysis.

Photoinduced electron transfer is an efficient approach to single-electron reduction of organic molecules for their activation. A variety of molecular photoredox systems have been developed for this purpose, whereas only a few of them exhibit potent …

Asymmetric Defluoroallylation of 4-Trifluoromethylpyridines Enabled by Umpolung C-F Bond Activation.

Carbon-fluorine bond activation reaction of the trifluoromethyl group represent an important approach to fluorine-containing molecules. While selective defluorofunctionalization reactions of CF3-containing substrates have been achieved by invoking …

Recent Developments in Transition-Metal-Free Functionalization and Derivatization Reactions of Pyridines.

Pyridine is an important structural motif that is prevalent in natural products, drugs, and materials. Methods that functionalize and derivatize pyridines have gained significant attention. Recently, a large number of transition-metal-free reactions …

An Umpolung Approach to the Hydroboration of Pyridines: A Novel and Efficient Synthesis of N-H 1,4-Dihydropyridines.

Umpolung of pyridine hydroboration was achieved by the reaction between pyridine and diboron(4) with a base and a proton source. , The first inverse hydroboration of pyridine with a diboron(4) compound and a …

Photoinduced Radical Borylation of Alkyl Bromides Catalyzed by 4-Phenylpyridine.

Utilizing pyridine catalysis, we developed a visible-light-induced transition-metal-free radical borylation reaction of unactivated alkyl bromides that features a broad substrate scope and mild reaction conditions. Mechanistic studies revealed a …

Visible-Light-Induced Organocatalytic Borylation of Aryl Chlorides.

The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the …

Super Electron Donors Derived from Diboron.

The combination of diboron, pyridine and base serves as an efficient source of structurally well-defined super electron donors. , Single-electron transfer is an important process in organic chemistry, in which a …