Herein, we report the synthesis of a benzimidazolylidene-stabilized borane adduct and its borenium ion. This borenium ion was used as a metal-free catalyst for hydrogenating various substituted quinoline N-heterocycles under ambient conditions. Furthermore, this method was utilized to synthesize two drug molecules: galipinine and angustureine. A detailed DFT study was performed to understand this metal-free catalytic hydrogenation
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.inorgchem.2c01841 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Mechanistic Insights into Ru-S Complex-Catalyzed C-H Silylation and Borylation of N-Heteroarene: Distinct Bonding Interactions.
Inorg Chem
March 2025
Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
The silylation and borylation of N-heteroarenes are essential processes for preparing key building blocks in organic synthesis. The Ru-S complex , [(PEt)Ru(DmpS)] (DmpS = 2,6-dimesitylphenyl thiolate), catalyzes both C-H silylation and borylation of N-heteroarenes. Herein, we performed a density functional study to investigate the mechanisms of catalyzed C-H silylation of 1-methylindole using hydrosilanes and C-H borylation using dialkoxyhydroborane (HBpin) and dialkylhydroborane (9BBN).
View Article and Find Full Text PDFA Borenium-Borane Composite for Exhaustive Reduction of Oxo-Chemicals.
J Am Chem Soc
January 2025
School of Chemistry and Chemical Engineering, Henan Key Laboratory of Boron Chemistry and Advanced Materials, Henan Normal University, Xinxiang, Henan453007,China.
Borenium ions have attracted significant attention in organic transformations due to their strong Lewis acidity. The reported borenium ions are often stabilized by sterically demanding substituents and strong coordination bonds. Herein, we have synthesized a small steric borenium-equivalent NHBHOTf and subjected it to the exhaustive reduction of a carboxylic functional group to a methyl group, which shows broad functional group tolerance.
View Article and Find Full Text PDFCompeting Photocleavage on Boron and at the -Position in BODIPY Photocages.
J Org Chem
January 2025
Department of Organic Chemistry and Biochemistry, Rud̵er Bošković Institute, Bijenička Cesta 54, Zagreb 10 000, Croatia.
BODIPY photocages (photocleavable protective groups) have stirred interest because they can release biologically active cargo upon visible light excitation. We conducted combined theoretical and experimental investigations on selected BODIPY photocages to elucidate the mechanism of the competing photocleavage at the boron and -position. Based on the computations, the former reaction involves elongation of the B-C bond, yielding a tight borenium cation and methyl anion.
View Article and Find Full Text PDFBorenium-Catalyzed "Boron Walking" for Remote Site-Selective Hydroboration.
J Am Chem Soc
January 2025
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
Article Synopsis
- Researchers have developed a new method for remote functionalization that uses a borenium ion as a catalyst instead of traditional transition metals, addressing issues like metal residue and catalyst poisoning.
- The process allows for site-selective modification of molecules by enabling the "walking" of a boron group along a carbon chain, ultimately favoring the formation of α-borylation products.
- This metal-free approach shows compatibility with various functional groups and can facilitate the synthesis of unique compounds, including those helpful in creating bioactive molecules.
Borenium Ion Equivalents Stabilized by BICAAC and Their Implementation as Catalysts in Hydrosilylation of Carbonyls.
Chemistry
January 2025
Department of Chemical Sciences, Indian Institute of Science Education and Research Mohali, Knowledge City, Sector 81, SAS Nagar, Mohali, Punjab, 140306, India.
Hydride abstraction from the borane adduct, (BICAAC) ⋅ BH afforded the hydride bridged dinuclear borenium ion equivalent complexes 1 and 2 that have been characterized by various spectroscopic and spectrometric techniques followed by the assessment of Lewis acidity using the Gutmann-Beckett method. The single crystal X-ray structure of complex 2 revealed the presence of discrete ions in the solid state. The complex (BICAAC) ⋅ BH(OTf) (3), obtained from the reaction of (BICAAC) ⋅ BH with MeOTf, formed the corresponding boronium cations [(BICAAC) ⋅ BH(L)](OTf) on reaction with Lewis bases (L= pyridine (4) and DMAP (5)).
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!