Charles Yeung

And here it is – Annulative Editing – aka The Monster Mash. What a super collab #PfizerChemistry & @sarponggroup.bsky.social
In 1 pot, activated pyrimidines with bis-nucleophiles like amino-pyrazoles & other small hets to deliver 6/5 hets and other useful products
#MyFirstJACS
#ChemSky #ChemChat

Accessing sulfonamides via formal SO2 insertion into C–N bonds - Nature Chemistry Despite recent advances in primary sulfonamide synthesis, approaches using primary amines as starting points for direct sulfonamide construction remain elusive. Now a formal SO2 insertion into the C–N...

Online today @natchem.nature.com - we show how to turn a deletion reaction into an insertion reaction:

www.nature.com/articles/s41...

Just out on ChemRxiv! We report a carbonylative ring expansion of cyclic carboxylic acids via a spin-center shift mechanism. This strategy provides modular access to valuable sp³-rich cyclic scaffolds from readily available carboxylic acids. chemrxiv.org/engage/chemr...

Carbon-Atom Scavengers Enable Divergent, Selective Carbon Deletion of Azaarenes Divergent synthesis is a powerful strategy that provides simultaneous access to multiple derivatives of a given substrate. However, the emerging developments in skeletal editing have largely delivered...

Our latest is a serendipitously discovered pair of reactions that can pull either the C2 or C3 carbon out of quinolines by choice of an amine scavenger. A deep mechanistic dive took us some surprising places, in @chemiejisoo.bsky.social's latest.

pubs.acs.org/doi/full/10....

If you're interested in a break from the doom-and-gloom, may I recommend our article, online today @nature.com

A solution to the pyrazole alkylation problem, leveraging S-to-NR atom replacement. Skeletal editing has strategic value, outside of late-stage!

www.nature.com/articles/s41...

Cheminformatic Analysis of Core-Atom Transformations in Pharmaceutically Relevant Heteroaromatics Heteroaromatics are the basis for many pharmaceuticals. The ability to modify these structures through selective core-atom transformations, or “skeletal edits”, can dramatically expand the landscape f...

Congrats to Logan & our collaborators Lucas (Sigman Group) & Reilly & @charlesthechemist.bsky.social (Merck) on the publication of our work on a cheminformatic analysis of core-atom transformations in pharmaceutically relevant heteroaromatics. Check it out in J. Med. Chem. now!

tinyurl.com/42re37pd

Phototransposition of Indazoles to Benzimidazoles: Tautomer‐Dependent Reactivity, Wavelength Dependence, and Continuous Flow Studies Herein, we report a detailed investigation of the photomediated transformation of indazoles to benzimidazoles through a nitrogen-carbon transposition. This phototransposition is known to occur in low....

Congrats to Logan, Sojung, Yusuke and collaborators from the Barner-Kowollik group, Gilead, and Merck on our indazole to benzimidazole conversion onlinelibrary.wiley.com/doi/10.1002/...
coordinated with the Leonori group onlinelibrary.wiley.com/doi/10.1002/...

oxygen and nitrogen insertion reactions into saturated carbocycles

Friends, I'm pleased to draw your attention to two new preprints today describing complementary heteroatom insertion reactions into saturated carbocycles, one from our group and another from the Knowles laboratory.

chemrxiv.org/engage/chemr...
chemrxiv.org/engage/chemr...

Really excited to see this amazing work out in ChemRxiv from our #ChemCollab between the @uwyoongroup.bsky.social @tehshik.bsky.social and #PfizerChemistry
Photochem-mediated oxygen migration into sp3 bonds delivering small ring ethers as well as an OH - methylene transposition
#ChemSky 1/

Two-Step Constitutional Isomerization of Saturated Cyclic Amines Using Borane Catalysis The prevalence of saturated azacycles within pharmaceuticals, natural products, and agrochemicals has prompted the development of many methods that modify their periphery. In contrast, technologies th...

Congratulations to Charis, Timothée, Giedre, Ryan, and visiting scholars Breanna and Julius as well as our collaborator Dr. Small on the publication of our work on the two-step isomerization of saturated cyclic amines, now on JACSAu!

pubs.acs.org/doi/10.1021/...

Interrogation of Enantioselectivity in the Photomediated Ring Contractions of Saturated Heterocycles We recently reported a chiral phosphoric acid (CPA) catalyzed enantioselective photomediated ring contraction of piperidines and other saturated heterocycles. By extruding a single heteroatom from a r...

Congratulations to Sojung, our collaborator from the Sigman group Jordan, our collaborators from Merck and former group members Justin and Yasuki on the publication of our work on understanding the enantioselectivity of our photomediated ring contraction in JACS!
doi.org/10.1021/jacs...

🚨 Exciting News! 🚨

What happens when unconventional ideas drive to push boundaries? 🚀 Meet FerroTACs: a novel #PROTAC design using ferrocene as core unit to re-imagining linker design and fine-tune their phys-chem properties. Learn more about our work led by @alesalerno.bsky.social here: 🧪👇 1/5

Alkene Carboxy-Alkylation via CO2•– Herein, we introduce a new platform for alkene carboxy-alkylation. This reaction is designed around CO2•– addition to alkenes followed by radical polar crossover, which enables alkylation through carbanion attack on carbonyl electrophiles. We discovered that CO2•– adds to alkenes faster than it reduces carbonyl electrophiles and that this reactivity can be exploited by accessing CO2•– via hydrogen atom transfer from formate. This photocatalytic system transforms vinylarenes and carbonyl compounds into a diverse array of substituted γ-lactone products. Furthermore, indoles can be engaged through dearomative carboxy-alkylation, delivering medicinally relevant C(sp3)-rich heterocyclic scaffolds. Mechanistic studies reveal that the active photocatalyst is generated in situ through a photochemically induced reaction between the precatalyst and DMSO. Overall, we have developed a three-component alkene carboxy-alkylation reaction enabled by the use of formate as the CO2•– precursor.

As part of our ongoing collaboration with @charlesthechemist.bsky.social at Merck, we found a new way to promote alkene carboxy-alkylation that exploits the unique chemoselectivity profile of CO2•- accessed from formate! Check it out! Also, first #ChemSky post! Congrats to all the authors!!!

Synthesis of Fused Bicyclic [1,2,4]-Triazoles from Amino Acids A 3-step modular procedure combining carboxylic acids with acyl hydrazines provides access to medicinally relevant [1,2,4]-fused triazoles. Good to excellent yields are achieved with tolerance of alip...

Semi-saturated heterocycles are super fragments in the med chem tool kit and now I. #JOC my #PfizerChemistry colleagues in La Jolla incl @joyann-donaldson.bsky.social with WuXi collaborators describe a repaid synth of 5/5 fused triazoles from simple staring materials pubs.acs.org/doi/10.1021/...

An image providing details of the award nomination process. The link in the post contains the same information

As my colleague David Thaisrivongs posted on LinkedIn: Attention chem grad students & postdocs: apply for the 2025 Merck Research Award for Underrepresented Chemists of Color! #MerckChemistry
Apply by Jan 17: survey.sogolytics.com/survey1.aspx...
Contact us at chemistsofcolor@merck.com #ChemSky

Would love to be added, thanks!

Stradiotto group PDF Kathleen Morrison just back from visiting our collaborator (Charles Yeung) at Merck to learn about HTE and to share her expertise on nickel catalysis 👍

A flexible and scalable synthesis of 4′-thionucleosides 4′-Thionucleosides (thNAs) are synthetic nucleoside analogues that have attracted attention as leads for drug discovery in oncology and virology. Here we report a de novo thNA synthesis that relies on...

So excited to see this published! Thionucleosides can be incredibly challenging to make due to the need for oxidation state changes at sulfur during the synthesis. Collaborating with the Britton group, we’ve been able to make them using a short, selective sequence!
pubs.rsc.org/en/content/a...

Tagging @sarponggroup.bsky.social!

Would love to be added! Thanks!

We wrapped 24' with a trip to Emory. Grateful to H. Davies for hosting & opening the event to the local community. Charles, Cecie, & Mel helped us pull it all off. The students were awesome, A. Walji told the Discovery story MK-0616 (molecule of the year), and J. Ellman (Imine) brought us home.

Please add me!

Implicit in my highlight here was a hope someone would do the same thing for skeletal editing and well...
chemrxiv.org/engage/chemr...

Very useful analysis - should spur lots more development in skeletal editing!

@charlesthechemist.bsky.social (Looks like Matt and Richmond aren't here yet?)

An Air-Stable, Single-Component Iridium Precatalyst for the Borylation of C–H Bonds on Large to Miniaturized Scales The functionalization of C–H bonds enables the modification of complex molecules, often with the intention of forming compound libraries. The borylation of aryl C–H bonds is a widely used class of C–H...

Definitely a must read Amazing work from the @HartwigGroup out in @J_A_C_S
Air stable Ir precat for C-H borylation with large scope and 1-pot Borylation-Suzuki, bromination or Chan-Lam
Super paper and will be of high use in med chem #ChemSky

Created a Starter Pack for Industry Chemists- let me know if you want in! #ChemSky