Our latest work shows how modern total synthesis can enable therapeutically meaningful discovery, uncovering selective anti-C. difficile activity and toxin-protective effects of structurally complex polyether ionophores. Now available on ChemRxiv: chemrxiv.org/doi/full/10.264…

In @Nature, we show that redox-active esters can be transformed into alkyl zinc species useful for transmetalation, providing a solution to rate matching in XEC reactions! First application: alkylation of alkenes via polar decarboxylative cross-coupling! nature.com/articles/s41586-0…

Nitrate reduction enables Sandmeyer reactions without sweat on your forehead – even on 20 mmol scale! Check out our detailed protocol in @OrgSynth and join us on the safer side of diazonium chemistry! Thanks to @MaulideLab for reproducing! 🤝 tinyurl.com/2h3earww

Making C-glycosides SWEET and simple! Today in @ChemRxiv we disclose (chemrxiv.org/doi/full/10.264…), in collaboration with @GroupAggarwal, an incredibly easy way to achieve radical functionalization of sugars. In this video (youtu.be/Fqdbgmx7zEI), a two-step synthesis of the billion dollar drug Dapagliflozin is achieved using household vinegar and dextrose powder from the local supplement store. High Level Summary: The work addresses a longstanding challenge in carbohydrate chemistry: the efficient, scalable, and stereocontrolled synthesis of C-aryl glycosides directly from unprotected native sugars. C-Aryl glycosides form the core pharmacophore of the SGLT2 inhibitors (dapagliflozin, canagliflozin, empagliflozin, and related agents), which are frontline therapies for type 2 diabetes and represent one of the highest-grossing classes of small-molecule drugs. Conventional synthetic routes to these molecules generally require extensive protecting-group manipulations, multi-step activation of glycosyl donors, or organometallic additions under demanding conditions. Recent advances in radical and transition-metal-catalyzed cross-couplings have improved access, yet most approaches still depend on protected precursors, specialized reagents, or protocols that are difficult to scale. We report a practical alternative based on glycosyl sulfonyl hydrazides—stable, crystalline radical precursors that are prepared in a single step from unprotected sugars by treatment with tosylhydrazine in acetic acid, followed by simple crystallization. These hydrazides undergo redox-neutral nickel-catalyzed radical cross-coupling with aryl iodides or bromides under mild conditions (70 °C, DMSO, tetramethylguanidine as base). The reaction requires no external oxidant or reductant, no photocatalyst, and no organotin species. In glucose-derived systems the coupling typically delivers high β-selectivity (>19:1 in many cases), an outcome that appears to depend on hydrogen-bonding interactions between tetramethylguanidine and the free hydroxyl groups. The main findings are as follows: All five FDA-approved SGLT2 inhibitors, as well as several clinical candidates, can be prepared in a single coupling step from the corresponding glycohydrazide. Decagram-scale synthesis of dapagliflozin was demonstrated starting from commercial dextrose; the product was isolated by aqueous workup and recrystallization (no column chromatography required at this scale). Di- and trisaccharides (lactose, cellobiose, maltose, maltotriose) couple directly to give aryl-linked oligosaccharides. Several natural products and medicinally relevant structures (salmochelin-SX, neopetrosin C, the tryptophan-mannose conjugate, and a ribose-derived IMPDH inhibitor) that previously required 9–20 steps or costly reagents are now accessible in 1–4 steps with good stereocontrol. The platform extends to non-anomeric C–C bond formation at positions C2–C6 on glucose and ribose scaffolds, providing the first systematic exploration of radical diversification across these positions. Stereoretentive radical cross-coupling, using configurationally pure hydrazides, enables programmable delivery of either α- or β-anomers, overriding inherent substrate biases and providing access to stereoisomers not previously obtainable by radical methods. The chemistry builds on our earlier development of sulfonyl hydrazide-based redox-neutral cross-coupling and stereoretentive radical arylation, here adapted and optimized for carbohydrate substrates. The method is operationally straightforward, uses inexpensive reagents and starting materials, and eliminates protecting-group strategies.

Our view on the recent @Nature publication of @dmacxh1 and co-workers! Continuing developments in deaminative chemistry are making the use of isolated diazonium salts more and more obsolete. Very exciting and great for lab safety! nature.com/articles/d41586-0…

Three-component assembly and structure–function relationships of (–)-gukulenin A by Vaani Gupta, Zechun Wang, Joshua B. Combs, Timothy Wright, Lei Chen, Boxu Lin, Ryan Holmes, Bo Qin, Joonseok Oh, Jason M. Crawford, and Seth B. Herzon @HerzonLab at @YaleChem in @ScienceMagazine science.org/doi/10.1126/scie…

Sendai is once again all dressed up for Tanabata! If you are downtown between Aug 6 - 8, look out for the beautiful decorations, including this special set hand-made by more than 70 Japanese and international students from Tohoku University! #tohokuuniversity #sendai #tanabata

📢 78 emplois menacés à Romainville chez Novalix ! Encore une casse de l’industrie du médicament, au mépris des salarié·es et de notre souveraineté sanitaire. À l’appel des salarié·es et des syndicats, je serai là pour les soutenir. ✊ RDV jeudi 17 juillet à 12h.

Finally returning back to Japan next November, almost 10 years after my last visit for my internship at Tohoku U. in the Y. Hayashi Lab. Can’t wait ! 😁 @LLemiegre

The nitrate reduction saga continues... Very happy that the 2nd follow-up paper of our nitrate reduction strategy is finally out in @J_A_C_S ! 🥳 open access 🔓 pubs.acs.org/doi/10.1021/jac…

A Mild & Efficient Route to Diazo Compounds! 🔎 Looking for a safe, scalable, and functionally tolerant method to convert azides into diazo compounds? Discover DPPS (1-[3-(Diphenylphosphino)-propanoyl]-2,5-pyrrolidindione)— a next-generation phosphine-based reagent engineered for modern organic synthesis. DPPS performs efficiently under mild conditions, such as in aqueous sodium bicarbonate, delivering excellent yields with high selectivity and minimal byproducts, while offering broad functional group compatibility and scalability for use in academic, biotech, and industrial research settings. 🔁 The reaction proceeds via acyl triazene intermediates, offering a clean fragmentation pathway and superior diazo compound formation — a key transformation in pharmaceuticals, agrochemicals, and materials science. 🎯 Whether you're working in click chemistry, diazo-transfer protocols, or carbene chemistry, DPPS offers a robust and reliable tool for your synthetic toolbox. 💡 Learn more about this method in the article onlinelibrary.wiley.com/doi/… 🛒 This reagent is available in our stock! enaminestore.com/catalog/EN3… Enamine offers a broad range of reagents and product subsets for organic synthesis that facilitate a wide variety of transformations. Explore all them here lnkd.in/gFMXnPKj #OrganicChemistry #ChemicalReagents #DiazoCompound #SyntheticChemistry #DrugDiscovery #ResearchTools #MedicinalChemistry #CarbeneChemistry #ChemistryReagents #ChemicalResearch #Enamine

Xanthopinacol Boronate: A Robust, Photochemically Assembled and Cleavable Boronic Ester for Orthogonal Chemistry (@angew_chem): onlinelibrary.wiley.com/doi/… @HallBoronLab).

Nitrate reduction meets palladium – in our new @angew_chem paper, we show how the generation of aryl diazonium salts as fleeting intermediates via nitrate reduction can be coupled with Pd-catalysis in a Suzuki-type cross coupling reaction! onlinelibrary.wiley.com/doi/…

Bonjour @LigneH_SNCF, pourquoi n’y a t il plus de trains origine St Leu la Forêt ce matin ? Merci d’avance et bonne journée

🚨Calling medicinal chemists🚨: A Suzuki het-het coupling sometimes does not require complex ligands. An air stable Ni would do. Amazing work from @rsaeb2 Rakan Saeb and Byeongdo Roh. onlinelibrary.wiley.com/doi/…

Bonjour @LigneH_SNCF, le train AFOI de 8h16 est il supprimé ? Prévu dans 2 mn au départ de St Leu, toujours aucun train à quai et pas d’infos… Merci d’avance

In our latest publication in @angew_chem we show how aryl thianthrenium salts can be used to access complex aryl diazoester at a late stage! 👀 Out now and open access! 🔓 Congrats to all involved! onlinelibrary.wiley.com/doi/…

Outstanding @HPJdeRouville 🌲!

Two Nobel in Chemistry in a row… what a sad end for 2024