The modular four-component carbonylation of unsaturated hydrocarbons represents an elegant strategy for the one-pot synthesis of complex carbonyl compounds. However, this strategy is currently focused on the 1,2-difunctionalization of olefins or alkynes, and the 1,4-alkylcarbonylation of 1,3-enynes remains unexplored. In this study, we report a Ni-catalyzed 1,4-alkylcarbonylation of CF3-containing 1,3-enynes under 1 atm of CO, which affords the tetra-substituted CF3-allenyl ketones with good yields and selectivity. This protocol features mild conditions, broad substrate scope, and acceptable functional group compatibility. Control experiments revealed that the reactivity of oxime esters (regulated by leaving groups) and polarity matching are crucial for the success of this four-component cascade. Preliminary mechanistic studies suggest that the acyl nickel complex is a key intermediate in this transformation. 

Nickel-Catalyzed Modular Four-Component 1,4-Alkylcarbonylation of 1,3-Enynes to Tetra-Substituted CF3–Allenyl Ketones

Hypervalent iodine compounds have found broad application in modern organic chemistry as reagents and catalysts. Cyclic hypervalent iodine reagents based on the benziodoxole heterocyclic system have higher stability compared to their acyclic analogues, which makes possible the preparation and safe handling of the reagents with special ligands such as azido, cyano, and trifluoromethyl groups. Numerous iodine-substituted benziodoxole derivatives have been prepared and utilized as reagents for transfer of the substituent on hypervalent iodine to organic substrate. Reactions of these reagents with organic substrates can be performed under metal-free conditions, in the presence of transition metal catalysts, or using photocatalysts under photoirradiation conditions. In this review, we focus on the most recent synthetic applications of cyclic hypervalent iodine(III) reagents with the following ligands: N3, NHR, CN, CF3, SCF3, OR, OAc, ONO2, and C(=N2)CO2R. The review covers literature published mainly in the last 5 years. 

Recent Progress in Synthetic Applications of Cyclic Hypervalent Iodine(III) Reagents

в начале 90-х годов ХХ в., ее основные положения непрерывно эволюционировали и развивались. На данный момент насчитывается 10–12 основных "краеугольных камней7quot;, на которых должен быть построен идеальный химический процесс. Данный обзор анализирует накопленный опыт и достижения на пути к созданию химических продуктов и процессов без использования или образования вредных веществ. Обзор представляет точку зрения ведущих российских специалистов, работающих в различных областях данного направления, включая гомогенный и гетерогенный катализ, тонкий и промышленный органический синтез, электрохимию, полимерную химию, химию на основе биовозобновляемого сырья, химию энергоемких соединений и материалов. Представлена также новая разработка российских авторов в области количественной оценки экологичности процессов. Библиография — 1761 ссылка.

The green chemistry paradigm in modern organic synthesis

A phosphine-free, efficient protocol for aminocarbonylation and carbonylative Suzuki-Miyaura coupling has been developed using a novel palladium complex, [PdII(DMAP)2(OAc)2]. The complex was successfully synthesized using a stoichiometric reaction between PdII(OAc)2 and DMAP in acetone at room temperature and characterized using single-crystal X-ray analysis. Only 5 mol % catalyst loading was sufficient for effective carbonylative transformations. "Chloroform-COware" chemistry was utilized for safe and facile insertion of the carbonyl unit using chloroform as an inexpensive CO source in a two-chamber setup. Various value-added pharmaceutically relevant compounds such as CX-516, CX-546, and farampator were synthesized using the technique. Furthermore, the commercially designed COware was engineered to COware-RB setup for sequential one-pot synthesis of indenoisoquinolines (topoisomerase I inhibitors).

Carbonylative Transformations Using a DMAP-Based Pd-Catalyst through Ex Situ CO Generation.

Incorporation of ZnO / Ag-ZnO nanoparticles into a cotton fiber by the LbL method for Self-Cleaning applications

A general and broadly applicable cobalt-catalyzed multicomponent 1,2-perfluoroalkylation carbonylation of alkenes has been developed. This protocol allows the synthesis of β-perfluoroalkyl-substituted amides, esters, and related derivatives using olefins, carbon monoxide, commercially accessible perfluoroalkyl iodides, and a variety of nucleophiles including low nucleophilic amides and urea derivatives in a one-pot manner. As an example, readily available trifluoroiodomethane can be utilized forming pharmaceutically relevant β-trifluoromethylated amides. To showcase the application potential, the perfluoroalkylation carbonylation process was applied to selected current drugs and biologically active molecules. The methodology permits a straightforward increase of the molecular complexity of olefins toward functionalized perfluoroalkylated building blocks in a regioselective manner. 

Cobalt-Catalyzed Multicomponent Carbonylation of Olefins: Efficient Synthesis of β-Perfluoroalkyl Imides, Amides, and Esters

In recent decades, the use of 1,3-butadiene as a comparably cheap and abundant raw material for new applications has attracted more and more interest, specifically in the chemical industry. The...

/pdf/industrially-applied-and-relevant-transformations-of-13-18fyqy96.pdf

Industrially Applied and Relevant Transformations of 1,3-Butadiene using Homogeneous Catalysts

Epitaxy and bonding of peelable ZnO film on graphene/ZnO substrate

Synthesis and structure elucidation of triarylmethyl radicals with anthryl substitution.

A visible-light-promoted and radical-mediated strategy for the site-specific cleavage of C(sp3)-C(sp3) bonds in ethers is reported. Different cyclic and linear alkyl ethers are converted into benzoylated acetals and aldehydes or...

Hypervalent-iodine Promoted Selective Cleavage of C(sp3)-C(sp3) Bonds in Ethers

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