A5052541038- Catalytic C–H Functionalization Methods
- Catalytic Alkyne Reactions
- Cyclopropane Reaction Mechanisms
- Synthesis and bioactivity of alkaloids
- Catalytic Cross-Coupling Reactions
- Computational Drug Discovery Methods
- Cancer therapeutics and mechanisms
- Cholinesterase and Neurodegenerative Diseases
- Synthesis and pharmacology of benzodiazepine derivatives
- Chemical synthesis and alkaloids
- Asymmetric Hydrogenation and Catalysis
- Asymmetric Synthesis and Catalysis
- Oxidative Organic Chemistry Reactions
- Synthesis of Organic Compounds
- Axial and Atropisomeric Chirality Synthesis
- Synthesis and Biological Activity
- Chemical Reactions and Isotopes
- Sulfur-Based Synthesis Techniques
Chulabhorn Research Institute
2018-2024
Scripps Research Institute
2022-2024
Ministry of Education
2019-2023
Chulabhorn Graduate Institute
2019-2023
A facile approach to obtaining densely functionalized cyclopropanes is described. The reaction proceeds under mild conditions via the directed nucleopalladation of nonconjugated alkenes with readily available pronucleophiles and gives excellent yields good anti-selectivity using I2 TBHP as oxidants. Pronucleophiles bearing a diverse collection electron-withdrawing groups, including −CN, −CO2R, −COR, −SO2Ph, −CONHR, −NO2, are well tolerated. Internal alkenes, which generally challenging...
We report a redox-neutral catalytic coupling of nitroalkanes and unactivated alkenes that proceeds by directed carbopalladation mechanism. The reaction is uniquely enabled the combination PdI2 as precatalyst HFIP solvent. Structurally complex nitroalkane products, including nitro-containing carbo- heterocycles, are prepared under operationally convenient conditions without need for toxic or corrosive reagents. Deuterium labeling experiments isolation catalytically relevant intermediate shed...
The ambiphilic reactivity of alkyl sulfonyl fluorides in the stereoselective synthesis diverse cyclopropanes from ole-fins under palladium(II) catalysis is presented. fluoride functionality serves as both an acidifying group and internal oxidant within ambiphile, enabling successive carbopalladation oxidative addition steps catalytic cycle, respectively. transformation grants access to cis-substituted exhibits broad compatibility with various fluorides, including those bearing –CN, –CO2R,...
Abstract A sequential synthesis of β‐naphthols and naphtho[2,3‐ b ]furan‐2(3 H )‐ones (naphthofuranones) has been developed using ortho ‐alkynylarylketones as the substrates. The AgTFA‐catalyzed ketonization generated corresponding 1,5‐diketone intermediates in situ; these were further cyclized via aldol condensation under basic conditions to obtain β‐naphthol products moderate good yields. For )‐ones, an additional lactonization step was applied give a broad range Moreover, this method also...
Eighteen hybrid compounds between 8-bromo-2-fluoro-isocryptolepine (4) and 1,2,3-triazole were synthesized via azide rearrangement-annulation reaction. Compound 4 underwent regioselective N-propargylation click reaction to form 8-bromo-2-fluoro-isocryptolepine-triazole hybrids 11 which evaluated for cytotoxic activity. c containing 1-anisyltriazole was the most effective in inhibiting HepG2, HuCCA-1 A549 cell lines (IC50 values of 1.65-3.07 μM) while a (1-phenyltriazole), j (1-para-CF3...
1,1-Disubstituted vinyl triflates are synthesized by direct hydrotriflation of terminal alkynes employing a combination TfOH and TMSN3 in DCM at room temperature. Interestingly, under these conditions, only were selectively converted to the corresponding triflates, while internal not reacted. A broad range substrates successfully 1,1-disubstituted good excellent yields even those with alkyne moieties present molecules.
A cascade oxazole-benzannulation for the synthesis of naphtho[2,3-d]oxazoles has been developed employing ortho-alkynylamidoarylketones as substrates. This procedure provides advantage preparing a wide variety substituents on naphtho[2,3-d]oxazole structures. In addition, o-alkynylamidoarylketones could be prepared from easily accessible and commercially available starting materials. Therefore, this method is judicious choice strategy to synthesize with great substituents. work, 27 examples...
Abstract Due to the rising prevalence of Alzheimer's disease (AD), there is a pressing need for more effective drugs treat or manage AD's symptoms. Studies have shown that cholinesterase inhibition can improve cognitive and behavioral symptoms associated with AD, by addressing cholinergic deficit. Based on recent development inhibitors indoloquinoline triazole moiety, we rationalized compounds an isocryptolepine‐triazole scaffold may also same biological targets. In this study, eighteen...
The generation of reactive carbocation intermediates from ortho-alkynylarylmethanol substrates was utilized as a means for the synthesis aryl(1-indanyl)ketones . Substrates with tertiary carbon at β-position to arene generated intermediate via dehydration/protonation, followed by cyclization and hydration give indanylketone products. For quaternary that position, protonation/elimination water, 1,2-shift subsequent cyclization/hydration highly substituted indanylketones.
A facile approach to densely functionalized cyclopropanes is described. The reaction proceeds under mild conditions via the directed nucleopalladation of non-conjugated alkenes with readily available pronucleophiles and gives excellent yields good anti-selectivity using I2 TBHP as oxidants. Pronucleophiles bearing a diverse collection electron-withdrawing groups, including–CN, –CO2R, –COR, –SO2Ph, -CONHR –NO2, are well tolerated. Internal alkenes, which generally challenging substrates in...
4-Acylchromene is an important core structure found in bioactive natural products and synthetic compounds. Moreover, this frequently used as a key precursor for the synthesis of more complex molecules. In work, we discovered that combination acetone catalytic I2 could lead to selective activation acetal alkynylarylether dimethylacetal substrates while alkyne moiety remained intact. This led generation oxonium ion intermediate which triggered intramolecular cyclization elimination methanol...
We report a redox-neutral catalytic coupling of nitroalkanes and unactivated alkenes that proceeds by directed carbopalladation mechanism. The reaction is uniquely enabled the combination PdI2 as precatalyst HFIP solvent. Structurally complex nitroalkane products, including nitro-containing carbo- heterocycles, are prepared under operationally convenient conditions without need for toxic or corrosive reagents. Deuterium labeling experiments isolation catalytically relevant intermediate shed...