A5100406492- Catalytic C–H Functionalization Methods
- Radical Photochemical Reactions
- Sulfur-Based Synthesis Techniques
- Plant-based Medicinal Research
- Bioactive Natural Diterpenoids Research
- Machine Learning in Materials Science
- Catalytic Cross-Coupling Reactions
- Oxidative Organic Chemistry Reactions
- Biological Activity of Diterpenoids and Biflavonoids
- Fluorine in Organic Chemistry
- Advanced Graph Neural Networks
- Phytochemistry and Biological Activities
- Computational Drug Discovery Methods
National Institute of Biological Sciences, Beijing
2019-2024
Peking University
2021-2024
As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C–C bonds. Here, we demonstrate that the combination of anodic preparation alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp2)–C(sp3) bonds, in which free aryl bromides—both readily available chemicals—can be directly used as coupling partners. This paired electrolysis...
A modular method for the acylation of aryl and alkyl halides is reported herein. The transformation relies on acylimidazoles, easy-to-prepare flexible species derived from abundant carboxylic acids, as viable cross-coupling partners Ni-catalyzed acylation. Careful examination revealed a remarkable mechanism: amide C–N bond primary secondary imidazolides can be activated by single-electron reduction, representing major departure other activation reactions. Extensive mechanistic studies also...
Structurally complex and bioactive ent-kaurane diterpenoids have well-characterized biological functions drawn widespread attention from chemists for many decades. However, construction of highly oxidized forms such still presents considerable challenges to synthetic chemists. Herein, we report the first total syntheses C19 oxygenated spiro-lactone ent-kauranoids, including longirabdiol, longirabdolactone, effusin. A concise synthesis common intermediate used all three was enabled via...
Here we report a general [3 + 2] radical annulation that allows the facile construction of bicyclo[3.2.1]octane motifs in ent-kaurane- and beyerane-type diterpenoids. This is difficult to control but was realized by harnessing an unprecedented counterintuitive effect TEMPO. Eleven natural products with wide array oxidation states are easily prepared, demonstrating powerful utility this straightforward synthetic strategy.
In this report, we describe a convergent paired electrochemical decarboxylative C(sp 2 )–C(sp 3 ) cross-coupling reaction that employs readily available alkyl carboxylic acids and )–iodides as direct coupling partners.
Although graph neural networks have achieved great success in the task of molecular property prediction recent years, their generalization ability under out-of-distribution (OOD) settings is still under-explored. Different from existing methods that learn discriminative representations for prediction, we propose a generative model with semantic-components identifiability, named SCI. We demonstrate latent variables this can be explicitly identified into semantic-relevant (SR) and...
Alkyl imidazolides were herein found to be viable coupling partners for the Ni-catalyzed acylation of aryl bromides. This cross-coupling reaction features a broad substrate scope and performed in an extremely cost-efficient fashion. Mechanistically, formation acyl radicals via reduction represents major departure from other reported radical reactions. Of particular note, extensive studies revealed intriguing chain mechanism remarkable CO-extrusion-recombination phenomenon. Finally,...