Truly never out of style! #JOrgChem celebrates the latest physical organic chemistry research with nearly 100 articles in this Special Issue. From quantum tunneling to catalyst design revealing how structure, energy, and environment drive reactivity!

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Call For Papers: Chemistry and Biology of Peptides | ACS Publications Chemistry Blog This Special Issue will celebrate the chemistry and biology of peptides, from synthesis, to structure and modifications, to biology and applications, and finally to degradation. Submit your manuscript...

Time is running out! ⏲️ Submit your manuscript by Dec 31 to #JOrgChem or #Biochemistry for this joint Special Issue featuring the chemistry and biology of peptides.

Learn more and submit here 👉 axial.acs.org/biology-and-...

🚨 Call for Papers!

Ready to reshape the future of organic synthesis? Submit to our Special Issue: “Skeletal Editing, Molecular Metamorphosis & Structural Reprogramming” jointly hosted by #OrgLett & #JOrgChem

📅 Deadline: June 1, 2026

axial.acs.org/organic-chem...

Nominate work for the #JOrgChem 2026 Outstanding Paper of the Year Award by Dec 31!

The award winner will receive:
- $2000 USD prize
- Complimentary travel and registration to ACS Fall 2026 in Chicago to deliver the award lecture
- Award plaque

americanchemical.co1.qualtrics.com/jfe/form/SV_...

[3 + 2] Annulation of Donor–Acceptor Cyclopropanes with Ammonium Thiocyanate: Interrupted Cascade Leads to Elusive Iminodihydrothiophene Derivatives A zinc iodide-mediated [3 + 2] cyclization between donor–acceptor cyclopropanes and ammonium thiocyanate has been developed to afford 2-imino-tetrahydrothiophene derivatives under mild conditions. Sub...

Another #EditorsChoice article published in #JOrgChem! Learn more about cyclopropane annulation to form elusive iminodihydrothiophene derivatives from Maity and co-workers

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Photo-Catalyzed Synthesis of Indanones from Aromatic Aldehydes and Terminal Alkynes Indanones are key structural motifs in pharmaceuticals and bioactive natural products, making their efficient synthesis a subject of continued interest. Conventional methods typically rely on transiti...

Read about this new photocatalyzed cyclization and HAT reaction published in #JOrgChem by Ghosh/Konig and coworkers. Selected for #EditorsChoice

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Reductive Amination Reactions Using Sodium Hypophosphite: a Guide to Substrates The reactions of reductive amination are of paramount importance as tools of synthetic organic chemistry. Recently, the applicability of sodium hypophosphite as a promising reductant for such reaction...

🆕 Catalyst free reductive amination with non toxic, cheap NaH₂PO₂!♻️

16 amine–carbonyl combos covered, tunable conditions & kinetic insights.

Check out the #JOrgChem guide to substrates📘

👉 doi.org/10.1021/acs....

@ChusovGroup @pubs.acs.org

Call For Papers: Chemistry and Biology of Peptides | ACS Publications Chemistry Blog This Special Issue will celebrate the chemistry and biology of peptides, from synthesis, to structure and modifications, to biology and applications, and finally to degradation. Submit your manuscript...

Do you work at the interface of chemistry and biology in the field of peptides? #JOrgChem and #Biochemistry have put out a Call for Papers related to all things peptides!

Submission deadline: Dec 31, 2025

axial.acs.org/biology-and-...

A very big congrats to the #JOrgChem winners of the Outstanding Publication of the Year Award, co-sponsored by the ACS Division of Organic Chemistry: Prof. Jacquelyne A. Read and colleagues!

axial.acs.org/organic-chem...

Check out our latest joint Special Issue between #JOrgChem and #OPRD: Excellence in Industrial Organic Synthesis! This is the third edition of this special issue highlighting the industrially relevant work in organic synthesis today.

pubs.acs.org/page/vsi/exc...

Call For Papers: Physical Organic Chemistry: Never Out of Style | ACS Publications Chemistry Blog This Special Issue will showcase the breadth of modern Physical Organic Chemistry and will set the stage for future innovation. Submit your manuscript by April 1, 2025.

Reminder! The deadline for submissions to the Physical Organic Chemistry special issue at #JOrgChem is coming up soon: April 1, 2025

axial.acs.org/organic-chem...

Polymer-Supported Selenium Affording Opportunities in Catalyst Design Polymer-supported selenium has been reported as a heterogeneous catalyst that is easily separated from the reaction system, thereby making the recovery and reuse of the catalyst more convenient. However, the utilization of polymer-supported selenium in the preparation of catalysts is not restricted to the aforementioned technical advantages. Recent studies have shown that polymer-supported selenium and small-molecule organoselenium catalysts have significant performance differences, leading to distinct reaction mechanisms, which offer more opportunities for the development of new organic reactions.

Find out more about polymer-supported selenium and organoselenium catalyst design in this recently published #JOrgChem JOCSynopsis! #Chemsky pubs.acs.org/doi/10.1021/...

This #JOrgChem cover art illustrates the rational protein engineering of the DERA enzyme from Geobacillus sp., resulting in two enantiocomplementary variants: (R)-selective DERAGeo-S185G and (S)-selective DERAGeo-T12I/S185A [ pubs.acs.org/doi/10.1021/... ] #Chemsky

Kobayashi’s Aryne Precursor for the One-Step Synthesis of Anthraquinones and Its Application to the Total Synthesis of Chrysophanol, Danthron, and Physcion A one-step synthetic method to access medicinally essential anthraquinones has been developed by reacting Kobayashi’s aryne precursors with 3-sulfonylphthalides following [4 + 2] Hauser–Kraus annulation reaction. The developed method has been implemented for the total synthesis of bioactive natural products, chrysophanol, danthron, and physcion in 30, 20, and 36% overall yields, respectively, from known compounds.

Excited to share that Barlalab groups' recent work has been accepted for publication in #JOrgChem. The authors acknowledge IISER_BERHAMPU and ANRFIndia for the financial support. #chemsky

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Multigram-Scale Synthesis of 2,5-Dideoxy-2,5-imino-d-mannitol (DMDP) and 2,5-Dideoxy-2,5-imino-d-glucitol (DGDP) from d-Fructose and l-Sorbose Using a Regioselective Appel Reaction We report a practical 5 g scale stereoselective synthesis of the valuable iminosugar DMDP from d-fructose in only 7 synthetic steps and in a 70% overall yield, which doubles previously reported yields. This process requires only two chromatographic purification steps, taking advantage of a regioselective Appel reaction. The regioselective reaction has also been applied on a similar scale to prepare the C-2 diastereomer of DMDP, DGDP, from l-sorbose in 7 steps (two purifications) and 56% overall yield, albeit with diminished diastereomeric purity (d.r. 90:10). The C-5 regioselectivity has also been illustrated on d-psicose and d-tagatose, making this an attractive method for preparing pyrrolidine iminosugars or 5-thiosugars from ketopyranoses.

Sunde-Brown and colleagues report a concise synthesis of the valuable iminosugars DMDP and DGDP on a multi-gram scale from D-fructose and L-sorbose via a regioselective Appel reaction #ChemSky #OpenAccess #JOrgChem pubs.acs.org/doi/10.1021/...

This week's #JOrgChem cover [ pubs.acs.org/toc/joceah/9... ] represents the elucidation of the Cope elimination mechanism using chemists’ tools: kinetic isotope effects (KIEs), linear free energy relationships (LFERs), and theoretical computations [ pubs.acs.org/doi/10.1021/... ] #chemsky

Organophotoredox-Driven Three-Component Synthesis of β-Trifluoromethyl β-Amino Ketones† In this work, we present a photoredox three-component reaction that enables the synthesis of medicinally relevant β-trifluoromethyl β-amino ketones from a N-trifluoroethylhydroxylamine derivative, styrenes and DMSO. Remarkably, fluoromethyl, difluoromethyl and pentafluoroethyl analogues are also accessed using the same reaction conditions. The mechanistic investigations, including radical trapping experiments, cyclic voltammetry, Stern–Volmer quenching studies and isotope labelling experiments support the photoinduced radical/polar crossover and Kornblum-type oxidation mechanisms. Finally, the applicability of the accessed organic skeletons is showcased by notable derivatization reactions.

Check out this photoredox three-component reaction for synthesizing relevant β-trifluoromethyl β-amino ketones. Fluoromethyl analogues included! Mechanistic insights + exciting derivatizations showcased #JOrgChem #chemsky

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Enantiodivergent Synthesis of Both (R)- and (S)-Heteroaryl Aldols by Rationally Engineered Aldolases Aldolases, especially 2-deoxyribose-5-phosphate aldolase (DERA) enzymes, have been widely employed to access key chiral precursors for various active pharmaceutical ingredients (APIs). This has been e...

Advancing Aldolase (DERA) for synthesis: Engineering DERA resulted in two enantiocomplementary variants. A single mutation switched enantioselectivity, enabling enantiodivergent synthesis of heteroaryl aldols in #JOrgChem #chemsky

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The cover of this week's issue of #JOrgChem [ pubs.acs.org/toc/joceah/9... ] features Schwarzites: hypothetical carbon allotropes made of heptagons or octagons with sp2 carbon atoms and having a negative Gaussian curvature [ pubs.acs.org/doi/10.1021/... ]

Synthesis of Enantiopure cis- and trans-Fused Octahydroisoindole-1-Phosphonic Acids from Octahydroisoindolones Phosphonic analogs of octahydroisoindole-1-carboxylic acids are bicyclic proline derivatives of interest in drug design and enzymatic mechanism studies. Here we report the stereoselective synthesis of...

Mario Ordóñez and José Luis Viveros-Ceballos are excited to present their recent work in #JOrgChem on the stereoselective synthesis of enantiopure cis- and trans-fused octahydroisoindole-1-phosphonic acids. Discover more below! #Chemistry #ChemSky
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The cover of this #JOrgChem issue illustrates the ceric ammonium nitrate (CAN)-mediated one-pot conversion process used to synthesize the natural product taiwaniaquinone H. #ChemSky

Cover article:
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JOC Issue:
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Silanediol-Bay-Bridge Rigidified Axially Chiral Perylene Bisimide Chiral organic molecules with a complementing π-structure are highly desired to obtain materials with good semiconducting properties and pronounced chirality effects in the visible region. Herein, we introduce a novel design strategy to achieve an axially chiral and rigid perylene bisimide (PBI) dye by attaching the chirality-inducing 2,2′-biphenoxy moiety at one side of the bay area and the rigidity-inducing di-tert-butylsilanediol bridge on the other side. This yielded a new bay-functionalized PBI derivative carrying the combination of a highly rigid and, simultaneously, an axially chiral perylene core. As a result, the derivative exhibits well-resolved absorption and emission spectra in the visible region, with a fluorescence quantum yield close to unity. Furthermore, the M- and P-enantiomers were found to be stable with a racemization barrier of 102 kJ mol–1 and, hence, could be successfully separated by chiral chromatography and studied by circular dichroism (CD) spectroscopy. This rigidified chiral-PBI could also be crystallized and analyzed by X-ray diffraction, showing the highest torsion angle of the perylene core with a value of up to 30.3° in the family of PBIs carrying the same di-tert-butylsilanediol bridge.

Check out this #EditorsChoice article in #JOrgChem: Silanediol-Bay-Bridge Rigidified Axially Chiral Perylene Bisimide by Frank Würthner and co-workers #ChemSky pubs.acs.org/doi/10.1021/...

Mechanisms of Activating Agents to Form Organozinc Reagents from Zinc Metal: Lessons for Reaction Design Activating agents enable the efficient preparation of organozinc complexes from zinc metal and organohalides, but their mechanisms had been obscured by the heterogeneous nature of these systems. Fluorescence microscopy, with the sensitivity to detect surface reaction intermediates, reveals distinct activating mechanisms of widely used activation strategies: trimethylsilyl chloride, LiCl, DMSO, and Rieke zinc powder. The resulting development of mechanistic models provides a better understanding of the oxidative-addition–solubilization sequence in organozinc reagent formation and contains lessons for methods development.

Check out this #EditorsChoice JOCSynopsis in #JOrgChem: Mechanisms of Activating Agents to Form Organozinc Reagents from Zinc Metal: Lessons for Reaction Design by Suzanne Blum and co-workers. Free to Read until July 2025! #ChemSky pubs.acs.org/doi/10.1021/...

This past week's cover of #JOrgChem features a calm natural setting which symbolizes the precision and control achieved through this catalytic process ( pubs.acs.org/doi/10.1021/... ), which holds promise for N,N,N-tridentate ligands ( pubs.acs.org/toc/joceah/8... ) #ChemSky

One-Pot Synthesis of Chiral Spiro-Imidazolidinone Cyclohexenones We have developed a simple and straightforward synthesis of chiral spiro-imidazolidinone cyclohexenones, featuring six contiguous stereocenters, from feedstock chemicals such as aminophenols, α,β-unsaturated aldehydes, and α-amino acids. Remarkably, this one-pot multicomponent reaction exhibits exceptional diastereoselectivity (>20:1 dr) and relies solely on an amino acid precursor as the chiral source, avoiding the use of transition metals or additional organocatalysts. This reaction is efficient and scalable, enabling synthesis on a gram-scale.

Efficient & green! 🌱 This one-pot synthesis of chiral spiro-imidazolidinone cyclohexenones (6 stereocenters, >20:1 dr) uses no metals or extra organocatalysts. Substrate = catalyst = sub-catalyst! By @dtdgroup in #JOrgChem #ChemSky pubs.acs.org/doi/10.1021/...

Synthesis of Spin-Labeled α-/β-Galactosylceramides and Glucosylceramides as Electron Paramagnetic Probes α-/β-Galactosylceramide (GalCer) and glucosylceramide (GlcCer) derivatives having a radical label at the 6-C-position suitable for electron paramagnetic resonance spectroscopic studies were synthesized by a diversity-oriented strategy that is highlighted by the efficient glycosylation of a lipid precursor and late-stage ceramide assembly to enable lipid diversification. The strategy was also utilized to synthesize natural α-/β-GalCers and GlcCers. Furthermore, the involved azido-intermediates are flexible platforms to access various other GalCer and GlcCer derivatives.

Rajendra Rohokale, Zhongwu Guo, et al. are excited to explore the rapid and modular synthesis of spin-labeled α-/β-galactosylceramides and glucosylceramides, which serve as fascinating electron paramagnetic probes! #JOrgChem #ChemSky pubs.acs.org/doi/10.1021/...

Open-Flask Protocol for the Removal of Alloc Carbamate and Allyl Ester Protecting Groups. Application to In-solution and On-resin Peptide Synthesis The standard protocol for Alloc group removal during peptide synthesis still presents limitations, including low reaction yields, N-allylated byproducts, and the use of air-sensitive Pd(PPh3)4. We addressed these challenges by developing a novel protocol using the air-stable Pd(PPh3)2Cl2 catalyst, Meldrum’s acid (MA), and triethylsilane (TES-H). This combination ensured high yields, eliminated N-allylated byproducts, and is compatible with automated synthesis. This cost-effective and efficient method shows promise for widespread use in peptide chemistry applications and beyond.

A simple new protocol for the removal of alloc carbamate and allyl esters that can be run in open flasks with a moisture stable catalyst--compatible with solid and solution phase peptide synthesis and can be used with traditional small molecules #JOrgChem #ChemSky pubs.acs.org/doi/10.1021/...

Electrophilic Intermediates in the Nef and Meyer Reactions: A Computational Study The generation, interconversion, and reactivity of electrophilic species generated upon activation of nitroalkanes with protic acids (the Nef and Meyer reactions) were investigated by quantum-chemical calculations. N,N-Bis(hydroxy)iminium (R2C═N+(OH)2) and N-oxoiminium (R2C═N+═O) cations were shown to be produced independently from aci-nitroalkanes, while N-hydroxynitrilium cations (RC≡N+–OH) were formed via nearly barrierless C–H bond cleavage in N-oxoiminium cations. The N-oxoiminium and N-hydroxynitrilium cations whose formation is favored under highly acidic anhydrous conditions are strong electrophiles capable of reacting even with nonactivated arenes under ambient conditions. The N-oxoiminium cations R2C═N+═O are highly unusual ambident species containing three contiguous electrophilic centers (C, N, and O atoms). Nucleophilic addition at the oxygen atom is less preferred than the C- and N-attack yet possible in an intramolecular variant. These computational results shed light on some key aspects of the mechanisms of the Nef and Meyer reactions and predict the possibility of numerous interrupted versions of these reactions.

New in #JOrgChem: Quantum chemical calculations of the Nef reaction mechanism reveal an unusual nitrosocarbenium ion possessing three contiguous electrophilic centers. Check out the research from @SukhorukovAlex Lab #ChemSky pubs.acs.org/doi/10.1021/...

Synthetic Access to l-Guluronic Acid via Fluorine-Directed C-5 Epimerization l-Guluronic acid is integral to the structures of alginates and to the pathogenesis of Pseudomonas aeruginosa. The exploitation of this hexose in both existing and new contexts is, however, limited by its prohibitively high commercial cost. We report on a short and efficient synthetic route to an l-GulA building block from a simple d-mannose thioglycoside. In this synthesis, the fluorine-directing effect is exploited to achieve a stereoselective C-5 epimerization. DFT calculations illuminate the substituent effects, which operate to confer this selectivity.

A modern Ferrier photobromination and F-directed reduction convert D-ManA to L-GulA, featuring a photochemical resolution to separate D- from L-products.
#ChemSky #glycotime #JOrgChem
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The cover of this #JOrgChem issue (created by Agata Nowak, University of the Arts Poznań, and Joanna Nowak-Karnowska) illustrates photocrosslinking reaction in DNA labeled with 5-fluoro-4-thiouridine

Issue: pubs.acs.org/toc/joceah/8...
Article: pubs.acs.org/doi/10.1021/...

#OpenAccess #ChemSky