Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
An expedient synthesis of α-aminoboronic acid derivatives via cobalt-catalyzed remote site-selective hydroboration of unactivated alkenes is described herein. The strategy is characterized by its simplicity, site-selectivity, and wide substrate scope, as both terminal and internal alkenes could undergo the reaction smoothly, affording the corresponding products in good yields. According to the mechanism, Co-H is generated from Co(acac) in the presence of HBpin, which starts the chain-walking strategy via a series of alkene insertion and β-H elimination process.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.5c00333 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of Remote C-N Diaxially Chiral Compounds via Cobalt-Catalyzed Atroposelective C-H Activation.
Org Lett
June 2025
College of Chemistry, Pingyuan Laboratory, Zhengzhou University, Zhengzhou 450001. China.
The construction of atropisomers bearing multiple stereogenic elements has attracted considerable interest, given their broad utility in asymmetric catalysis, pharmaceuticas, and functional materials. Herein, we report a highly efficient cobalt-catalyzed atroposelective C-H activation-annulation reaction that simultaneously establishes two remote C-N chiral axes in a single operation. This approach proceeds under oxygen conditions by using a commercially available cobalt(II) catalyst in conjunction with a chiral salicyloxazoline (Salox) ligand.
View Article and Find Full Text PDFAtroposelective Synthesis of Pyridoindolones Bearing Two Remote Distinct C-N Axes through Cobalt-Catalyzed Enantioselective C-H Activation.
J Am Chem Soc
March 2025
Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310058, China.
C-N axially chiral compounds represent an important class of atropisomers that are prevalent in bioactive and material molecules. Despite recent advances in synthetic methodologies, the asymmetric construction of atropisomers featuring multiple C-N axes has been rarely explored, significantly limiting their further applications. Herein, we report a novel atroposelective synthesis of diaxially chiral pyridoindolones featuring both six-five and six-six C-N axes through cobalt-catalyzed asymmetric C-H annulation.
View Article and Find Full Text PDFCobalt-Catalyzed Remote Site-Selective Hydroboration of Unactivated Alkenes via Chain-Walking Strategy.
Org Lett
March 2025
Institute of Next Generation Matter Transformation, College of Material Sciences Engineering, Huaqiao University, Xiamen, Fujian 361021, China.
An expedient synthesis of α-aminoboronic acid derivatives via cobalt-catalyzed remote site-selective hydroboration of unactivated alkenes is described herein. The strategy is characterized by its simplicity, site-selectivity, and wide substrate scope, as both terminal and internal alkenes could undergo the reaction smoothly, affording the corresponding products in good yields. According to the mechanism, Co-H is generated from Co(acac) in the presence of HBpin, which starts the chain-walking strategy via a series of alkene insertion and β-H elimination process.
View Article and Find Full Text PDFEnantioselective Cobalt-Catalyzed Remote Hydroboration of Alkenylboronates.
Org Lett
February 2025
College of Pharmacy, Guizhou Engineering Laboratory for Synthetic Drugs, Guizhou University, Guiyang, Guizhou 550025, People's Republic of China.
Heteroatomic groups in alkenes typically direct thermodynamically favored chain walking of C═C bonds toward themselves, thereby facilitating C-H bond functionalization near the heteroatoms. We present herein an efficient cobalt-catalyzed contra-thermodynamic remote hydroboration of alkenylboronates with pinacolborane to synthesize chiral 1,-diboronates. This protocol features a broad substrate scope, high functional group tolerance, and excellent enantioselectivity.
View Article and Find Full Text PDFCoH-catalyzed asymmetric remote hydroalkylation of heterocyclic alkenes: a rapid approach to chiral five-membered S- and O-heterocycles.
Chem Sci
June 2024
Frontiers Science Center for Flexible Electronics (FSCFE), Shaanxi Institute of Flexible Electronics (SIFE), Shaanxi Institute of Biomedical Materials and Engineering (SIBME), Northwestern Polytechnical University (NPU) 127 West Youyi Road Xi'an 710072 China
Saturated heterocycles, which incorporate S and O heteroatoms, serve as fundamental frameworks in a diverse array of natural products, bioactive compounds, and pharmaceuticals. Herein, we describe a unique cobalt-catalyzed approach integrated with a desymmetrization strategy, facilitating precise and enantioselective remote hydroalkylation of unactivated heterocyclic alkenes. This method delivers hydroalkylation products with high yields and excellent stereoselectivity, representing good efficiency in constructing alkyl chiral centers at remote C3-positions within five-membered S/O-heterocycles.
View Article and Find Full Text PDF