Saturated bicyclic compounds make up a valuable class of building blocks in the development of agrochemicals and pharmaceuticals. Here, we present the synthesis of borylated bicyclo[2.1.1]hexanes via crossed [2 + 2]-cycloaddition. Due to the presence of the C-B bond, a variety of structures can be easily prepared that are not accessible by other methods. Moreover, a rare photo-ene reaction is also disclosed, allowing for the diastereoselective synthesis of trisubstituted borylated cyclopentanes.
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http://dx.doi.org/10.1021/jacs.4c01557 | DOI Listing |
Org Lett
January 2025
Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, College of Chemistry & Chemical Engineering, Anhui University, Hefei, Anhui 230601, China.
Boron compounds are widely employed in organic chemistry, pharmaceuticals, and materials science. Among them, borylated heterocycles serve as versatile synthons for the construction of new C-C or C-heteroatom bonds via coupling or radical processes. Such methods for direct C-H borylation reactions are of high synthetic value to reduce the number of synthetic steps and the amount of waste and to improve efficiency.
View Article and Find Full Text PDFChemistry
January 2025
INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH PUNE, CHEMISTRY, HOMI BHABA ROAD, PASHAN, PUNE, 411008, PUNE, INDIA.
In this work, we have reduced CO2 with HBpin to afford borylated methanol product selectively in ~99% yield using Ce[N(SiMe3)2]3(THF)3 as a catalyst. This led to multigram scale isolation of methanol obtained from CO2 reduction via the hydrolysis of borylated methanol, this establishes the potential of Ce[N(SiMe3)2]3(THF)3 as an efficient homogeneous catalyst for the bulk scale methanol synthesis. A practical application of this catalytic system was also shown by reducing CO2-containing motorbike exhaust efficiently and selectively.
View Article and Find Full Text PDFMolecules
December 2024
Institute of Organic Chemistry and Macromolecular Chemistry, Faculty of Mathematics and Natural Sciences, Heinrich Heine University Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany.
(3-(pyrimidin-4-yl)-7-azaindoles) are synthetic hybrids of the naturally occurring alkaloids and and display a strong cytotoxic potential. We have recently shown that the novel derivative is highly cytotoxic in several lymphoma and leukemia cell lines as well as in primary patient-derived lymphoma and leukemia cells and predominantly targets cyclin-dependent kinases (CDKs). Here, we efficiently synthesized nine novel 2-aminopyridyl congeners (-), i.
View Article and Find Full Text PDFInorg Chem
January 2025
Department of Chemistry, University of Richmond, Richmond, Virginia 23173, United States.
Copper(I) complexes of isobutyl- () and isopropyl-substituted () proazaphosphatranes have been synthesized. Structural and computational studies of a series of monomeric complexes CuX (X = Cl, Br, I) and dimeric [CuCl] provide insight into the transannulation within and steric properties of the proazaphosphatrane ligand. These halide complexes are competent precatalysts in a model borylation reaction, and the silylamido complex CuN(TMS) catalyzes hydrosilylation of benzaldehyde under mild conditions.
View Article and Find Full Text PDFACS Appl Mater Interfaces
January 2025
School of Chemistry & Chemical Engineering, Henan University of Science and Technology, Luoyang, Henan 471023, People's Republic of China.
The sensitive and selective identification of nitroaromatic explosives and industrially ubiquitous nitrates, which are harmful to the environment, is crucial from the viewpoints of security and environmental remediation. New multifunctional fluorescent porous materials that can sense nitro-explosives and nitrates are under continuous development. To this end, this study synthesizes 3,10,15-/-3,10,16-tribromotrinaphtho[3.
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