A5079048867- Synthetic Organic Chemistry Methods
- Chemical Synthesis and Analysis
- Catalytic Cross-Coupling Reactions
- Marine Sponges and Natural Products
- Asymmetric Synthesis and Catalysis
- Innovative Microfluidic and Catalytic Techniques Innovation
- Asymmetric Hydrogenation and Catalysis
- Catalytic C–H Functionalization Methods
- Evaluation Methods in Various Fields
- Radical Photochemical Reactions
- Water Treatment and Disinfection
- Oxidative Organic Chemistry Reactions
- Cyclopropane Reaction Mechanisms
- Sulfur-Based Synthesis Techniques
- Machine Learning in Materials Science
- Chemistry and Chemical Engineering
- Membrane Separation Technologies
- Fish Biology and Ecology Studies
- Adsorption and biosorption for pollutant removal
- Environmental Changes in China
- Synthesis and Catalytic Reactions
- Research studies in Vietnam
- Polyamine Metabolism and Applications
- Pharmaceutical and Antibiotic Environmental Impacts
- Traditional and Medicinal Uses of Annonaceae
Novartis (Switzerland)
2021-2025
Novartis (China)
2019-2024
Huahai Pharmaceutical (China)
2024
Changshu Institute of Technology
2021
Harvard University
2017
State Key Joint Laboratory of Environment Simulation and Pollution Control
2016
Beijing Normal University
2016
Hong Kong University of Science and Technology
2013
University of Hong Kong
2013
Nanjing University of Posts and Telecommunications
2009
A sustainable C(sp 2 )–C(sp 3 ) cross-electrophile coupling was developed between readily available 5-bromophthalide and 1-benzyl-4-iodopiperidine under micellar conditions, leading to a key intermediate of one our development compounds.
It is shown here for the first time that diethyl azodicarboxylate promotes dehydrogenation of tertiaryamines to afford enamines, which subsequently take place in tandem reactions with sulfonyl azides give N-sulfonyl amidine derivatives. A number different substituted and can successfully be coupled, several functionalized groups are tolerated this system. The reaction described mild, general, efficient, thus providing an extremely preferable method synthesis a variety
With a growing toolbox of surfactant-mediated chemistry in water and an increased number scaled-up transformations has come tremendous learning [for example, see: Lipshutz, B. H.; et al. The Hydrophobic Effect Applied to Organic Synthesis: Recent Synthetic Chemistry "in Water". Chem. - Eur. J. 2018, 24 (26), 6672–6695]. These opportunities now reside within few expert groups, while all the details are far from fully understood or still under development, substantial know-how been gained both...
The rapid emergence of large language model (LLM) technology presents significant opportunities to facilitate the development synthetic reactions. In this work, we leveraged power GPT-4 build a multi-agent system handle fundamental tasks involved throughout chemical synthesis process. comprises six specialized LLM-based agents, including Literature Scouter, Experiment Designer, Hardware Executor, Spectrum Analyzer, Separation Instructor, and Result Interpreter, which are pre-prompted...
Abstract A zirconium/nickel‐mediated one‐pot synthesis of ketones is reported. In the presence Zn or Mn, Cp 2 ZrCl was found to dramatically accelerate coupling and suppress side product formation via an I→SPy displacement at same time. Unlike Zn/Pd‐ Fe/Cu‐mediated ketone syntheses, new method effective for nucleophiles bearing OR equivalent functional groups α‐position. mechanism comprising a nickel catalytic cycle, zirconium Zr→Ni transmetalation proposed, and/or low‐valent Zr species are...
The formation of sterically hindered C(sp2)-C(sp3) bonds could be a useful synthetic tool but has been understudied in cross-electrophile coupling. Here, we report two methods that couple secondary alkyl bromides with aryl halides contain C-X bonds: 1) ortho-substituted nickel catalysts and 2) di-ortho-substituted iodides cobalt catalysts. Stoichiometric experiments deuterium labeling studies show [Co] is better than [Ni] for oxidative addition Ar-I radical capture/reductive elimination...
The technology of surfactant chemistry is employed for amide bond construction via the reaction acyl chlorides with amines in 2 wt % TPGS-750-M aqueous solution. Specifically, this highly efficient method enables a chromatography-free scalable process and recycling
Abstract Unified, efficient, and scalable syntheses of the halichondrin natural products are reported. A newly developed Zr/Ni‐mediated one‐pot ketone synthesis was used to couple two halves final product at a late stage in synthesis. With use slight excess left halves, desired ketones were isolated yields 80–90 %. The halichondrins obtained from these steps, namely desilylation [5,5]‐spiroketal formation. new synthetic route effective for total all members homohalichondrin subgroup....
Nitrogen heterocycles are commonly found in bioactive natural products and drugs. However, the biocatalytic tools for nitrogen heterocycle synthesis limited. Herein, we report discovery of vanillyl alcohol oxidases (VAOs) as efficient biocatalysts one-pot 2-aryl thiazolines from various 4-hydroxybenzaldehydes aminothiols. The wild-type biocatalyst features a broad scope 4-hydroxybenzaldehydes. Though aminothiols is limited, it could be improved via semi-rational protein engineering,...
The rapid emergence of large language model (LLM) technology presents promising opportunities to facilitate the development synthetic reactions. In this work, we leveraged power GPT-4 build an LLM-based reaction framework (LLM-RDF) handle fundamental tasks involved throughout chemical synthesis development. LLM-RDF comprises six specialized agents, including Literature Scouter, Experiment Designer, Hardware Executor, Spectrum Analyzer, Separation Instructor, and Result Interpreter, which are...
Abstract The 9‐methoxy‐9‐borabicyclo[3.3.1]nonane‐based B ‐alkyl Suzuki–Miyaura cross‐coupling reaction (the 9‐MeO‐9‐BBN variant) has been efficiently performed by using the catalyst consisting of Pd(OAc) 2 and a hemilabile P,O‐ligand, Aphos‐Y, under mild conditions (K 3 PO 4 · 3H O, THF/H room. temp.). For applications in total synthesis structurally complex natural products, Johnson protocol commonly uses two ligands (dppf Ph As) organic solvents (THF DMF). In contrast, new version...
A robust and sustainable C(sp<sup>2</sup>)–C(sp<sup>3</sup>) cross-electrophile coupling was developed <italic>via</italic> nickel/copper synergistic catalysis under micellar conditions.
A stereocontrolled synthesis of the left halves halichondrins was reported. An intramolecular oxy-Michael reaction under basic conditions used to construct [6,6]-spiroketal in a manner. With this approach, halichondrins, homohalichondrins, and norhalichondrins were synthesized.
The right halves of halichondrins A-C were synthesized by coupling the common C20-C37 building block 9 with C1-C19 blocks 10a-c, respectively. Catalytic, asymmetric Ni/Cr-mediated was used for three C-C bond formations. For all cases, stereochemistry controlled Cr catalyst prepared from chiral sulfonamide identified via toolbox approach. (3 + 4)-, (6 7)-, and (9 10)-couplings, stereoselectivity 28:1, >40:1, ∼20:1 achieved catalysts (S)-H, (S)-I, (R)-L, Unlike first second couplings, third...
A web-based application that can autonomously analyze the risk category of N -nitrosamine compounds from their SMILES notation, providing instant screening to identify high-risk formations -nitrosamines.
Abstract A zirconium/nickel‐mediated one‐pot synthesis of ketones is reported. In the presence Zn or Mn, Cp 2 ZrCl was found to dramatically accelerate coupling and suppress side product formation via an I→SPy displacement at same time. Unlike Zn/Pd‐ Fe/Cu‐mediated ketone syntheses, new method effective for nucleophiles bearing OR equivalent functional groups α‐position. mechanism comprising a nickel catalytic cycle, zirconium Zr→Ni transmetalation proposed, and/or low‐valent Zr species are...
Nitrosamine drug substance-related impurities (NDSRIs), which are compounds that can form during certain manufacturing processes and have been shown to cause cancer, assessing mitigating their formation has become an important public health issue as evidenced by recent guidelines from authorities like the FDA EMA provide acceptable intake limits for various N-nitrosamines. We developed a web-based application autonomously analyze N-nitrosamine risk category of SMILES notation, providing...
Abstract Unified, efficient, and scalable syntheses of the halichondrin natural products are reported. A newly developed Zr/Ni‐mediated one‐pot ketone synthesis was used to couple two halves final product at a late stage in synthesis. With use slight excess left halves, desired ketones were isolated yields 80–90 %. The halichondrins obtained from these steps, namely desilylation [5,5]‐spiroketal formation. new synthetic route effective for total all members homohalichondrin subgroup....
Abstract Nitrogen heterocycles are commonly found in bioactive natural products and drugs. However, the biocatalytic tools for nitrogen heterocycle synthesis limited. Herein, we report discovery of vanillyl alcohol oxidases (VAOs) as efficient biocatalysts one‐pot 2‐aryl thiazolines from various 4‐hydroxybenzaldehydes aminothiols. The wild‐type biocatalyst features a broad scope 4‐hydroxybenzaldehydes. Though aminothiols is limited, it could be improved via semi‐rational protein engineering,...
An environmentally sustainable approach for the Hofmann rearrangement was developed. The presence of nanomicelles allows such a transformation to proceed smoothly in mild conditions with water as sole reaction medium compared traditional methods, which use significant amounts organic solvents. A variety amides containing functional groups have been constructed under these conditions, affording compounding amine product good excellent yields (up 99%). process scaled up and proven be robust...
The development of a safe, efficient and scalable continuous‐flow‐chemistry protocol for the O‐difluoromethylation two 3‐hydroxypyridine building blocks is described. This example highlights that continuous flow chemistry has become firmly established within Novartis Biomedical Research, when implemented appropriately can enable supply material from first realization potentially interesting intermediate discovery project all way through to clinical evaluation.