Dong Group at UChicago

By merging this method with carbonyl migration and established C–H oxidation chemistry, we are now able to apply nitrogen scanning in saturated systems!

Check out our recent work on aliphatic C-to-N atom swap enabled by NAHA chemistry! This strategy enables access to diverse saturated N-heterocycles from cyclic ketones or cyclic alkanes. See: chemrxiv.org/engage/chemr...

This weekend, we had a wonderful Christmas & New Year party with our group!
Many thanks to Guangbin for hosting and bringing everyone together. Wishing the Dong group a joyful holiday season and a great year ahead!

These shape-shifting rings create customizable cores 1,2-oxaborines can shift into 11 different ring shapes to make modifying molecular cores easy

Thrilled to see our recent Nature Chemistry work featured in
@cenmag.bsky.social !
Big thanks to @bribarbu.bsky.social for the great coverage!

Core diversification using 1,2-oxaborines as a versatile molecular platform Nature Chemistry - In drug discovery, the preparation of analogues with diverse core structures often requires laborious efforts. Now it has been shown that 1,2-oxaborines, which are synthesized...

Check out our latest work in Nat. Chem. @natchem.nature.com !
We developed a platform using 1,2-oxaborines to construct a broad range of aromatic and non-aromatic cores from common enone/enal precursors.
Congratulations to Yao and the team!
Read here: rdcu.be/eJ90T

“Cut-and-Sew” Reactions of β-Lactams via C–C Bond Activation Transition metal-catalyzed “cut-and-sew” reactions offer an efficient approach to construct bridged and fused scaffolds; however, the substrates have been primarily restricted to cyclic ketones and ac...

Developed by Liyan and Rui, we expand our cut-and-sew chemistry to β-lactams, enabling access to diverse bridged & fused N-heterocycles. Now online in @jacs.acspublications.org ! Congratulations to the team!
pubs.acs.org/doi/full/10....

Site-selective Ru-catalysed saturation of unactivated arenes via directed 6π activation Nature Catalysis - Directing group strategies for selective dearomatization of unactivated aromatic π-systems have remained elusive. Now a homogeneous ruthenium catalyst, aided by a removable...

Check out our recent Nature Catalysis@natcatal.nature.com work on ruthenium-catalysed site-selective arene saturation—turning flat arenes into 3D sp³ frameworks!
👏Congrats to Congjun@congjun.bsky.social and the team!
Read here: rdcu.be/eCQQB

Advances in vicinal dicarbo-C–H-functionalization of five-membered heteroarenes via palladium/norbornene cooperative catalysis Direct introduction of two carbon substituents to less functionalized aromatic cores has been an attractive objective for late-stage modification and …

Our latest achievement is now online in Tetrahedron Letters, published as part of a special issue honoring Prof. Song Lin @songlin1.bsky.social for receiving the Tetrahedron Young Investigator Award.
sciencedirect.com/science/arti...
Congratulations to Xin and all co-authors!

Last weekend, we had a wonderful farewell party for Congjun and Miao at Guangbin's house.
Congjun will join UC Boulder as a tenure-track Assistant Professor, and Miao will be starting at Merck as a Senior Scientist.
Wishing them both the best of luck!

N‐methylbicyclo[2.2.1]hept‐2‐ene‐2‐carboxamide [2394994-09-1] C9H13NO (MW 151.21) InChI = 1S/C9H13NO/c1-10-9(11)8-5-6-2-3-7(8)4-6/h5-7H,2-4H2,1H3,(H,10,11) InChIKey = BYXAMVZFVXOYIF-UHFFFAOYSA-N (reagent used as a co-catalyst...

Proud to add one more reagent to EROS!
In this article, we summarized the synthesis and application of the N-methylbicyclo[2.2.1]hept-2-ene-2-carboxamide, a co-catalyst in the palladium/norbornene cooperative catalysis.
Congrats to Dr. Shinyoung Choi!
onlinelibrary.wiley.com/doi/10.1002/...

Enantioconvergent carbenoid insertion into carbon–boron bonds Nature Synthesis - An enantioconvergent approach for direct asymmetric insertion of racemic carbon-, oxygen-, nitrogen-, sulfur- and silicon-substituted carbenoids into carbon–boron bonds is...

🔥 Scalable achievement in enantioselective homologation.
🔥 Our work on "Enantioconvergent carbenoid insertion into carbon−boron bonds" is now online on Nature Synthesis rdcu.be/etopg
🎉Congratulations to Qiqiang!
🙏Thanks to our collaborator Liu group

Toward Iridium-Catalyzed Asymmetric Branched-Selective α-Alkylation of Aldehydes with Unactivated Alkenes Enabled by a Pyrazole Mediator Aldehyde α-alkylation remains a challenging transformation. On the other hand, given the wide availability of alkenes, it has been an attractive objective to use unactivated alkenes as alkylating agen...

🚀New advance toward asymmetric α‑Alkylation of Aldehydes.
✨Lead by Kezhi, we report a branched-selective α-alkylation of aldehydes with unactivated olefins — enabled by a pyrazole mediator and a chiral Ir catalyst. Congrats!
pubs.acs.org/doi/full/10....

🚨Just out in Nature!
We have offered a general method for 1,2-difunctionlization of arenes via a differential 1,2-diborylation!
rdcu.be/esXq8
www.nature.com/articles/s41...
Congratulations to Jingfeng!

How do you turn a carbonyl into sulfur?

In this work, Zining from our lab developed a carbonyl-to-sulfur swap enabled by a rationally designed N′-alkyl-hydrazonamide (NAHA) reagent that promotes double C-C bond activation.

www.science.org/doi/10.1126/...

Carbonyl-to-sulfur swap enabled by sequential double carbon-carbon bond activation In drug development, replacement of a skeletal carbon with a sulfur atom can result in analogs of bioactive compounds with improved properties. Currently, the sulfur analogs are almost exclusively pre...

Out First Release in @science.org today, Zining Zhang in @donglab.bsky.social swaps out ketones for sulfur in saturated carbon rings through two modes of radical trapping www.science.org/doi/10.1126/...

Downsizing lactams via Rh-catalyzed C–C activation Ring-contraction reactions are valuable transformations to access harder-to-synthesize smaller-sized rings from more-available larger-sized precursors…

Thrilled to share our latest achievement in C-C activation: Downsizing lactams via Rh-catalyzed C-C activation.
www.sciencedirect.com/science/arti...
Congratulations to Rui and Kangmin!

Alkyl Fluoride Synthesis via Cu-Mediated Deacetylative Fluorination Given the increasing demand for diverse alkyl fluorides for various applications, it would be beneficial to enrich the fluorination toolbox by including more kinds of common functional groups, such as ketones, as fluoride surrogates. Here we report a Cu-mediated deacylative fluorination approach that can convert a wide range of methyl ketones to the corresponding alkyl fluorides. The reaction is enabled by a ketone activation reagent and a nucleophilic fluoride source. It features broad functional group tolerance, capability for the late-stage fluorination, fluoro-annulation, synthesis of α,α-dideuterated fluorides, and degree-controlled synthesis of mono-, di-, and trifluoro alkanes from a single ketone starting material. The computational studies suggest interesting Cu(III)-mediated C–F bond forming pathways via either fluorine atom transfer or an SN2 process.

So excited to share a new achievement by Zining and Kezhi in collaboration with Prof. Peng Liu!!! We developed a Cu-mediated deacylative fluorination approach that can convert a wide range of methyl ketones to the corresponding alkyl fluorides.
pubs.acs.org/doi/full/10....

Atom-by-Atom Iterative Synthetic Logic: Laying the Foundation for Programmable Automated Construction of Small Organic Molecules Fully automated preparation of diverse small organic molecules remains a formidable challenge due to the inherent constraints of conventional synthetic philosophies. The existing automation approaches require access to either almost unlimited kinds of chemical reagents or custom-made building blocks (BBs). Herein we propose atom-by-atom iterative synthesis (AIS) as a new synthetic logic to tackle this challenge. By viewing complex organic molecules as assemblies of single-carbon- or heteroatom-based units, AIS aims to construct molecular skeletons through iterative coupling of simple atomic-scale BBs by a unified type of reaction─boron homologations. Compared with conventional approaches, the AIS strategy uses only a few types of chemical reactions and a small set of BBs, making it more suitable for automation and artificial intelligence-assisted synthetic route design. To date, enormous progresses have been made on the synthetic chemistry that serves for the purpose of AIS, such as introducing heteroatoms and sp2-carbons, forming ring structures, developing thermostable carbenoid reagents, and achieving stereochemical controls. On the other hand, substantial challenges and limitations remain to be overcome for realizing fully automated construction of diverse molecules. This Outlook article describes the AIS concept, recent progress, current limitations, and future opportunities in this field.

Please check out our recent outlook written by Miao:
Atom-by-Atom Iterative Synthetic Logic: Laying the Foundation for Programmable Automated Construction of Small Organic Molecules | ACS Central Science pubs.acs.org/doi/10.1021/...

A big thanks to all the authors and the incredible Pd/NBE community for pushing the boundaries of this powerful platform. Looking forward to many more innovative and impactful transformations in the future!

Excited to share that “Palladium and Norbornene Cooperative Catalysis: Fundamentals and Applications”—edited by Guangbin—is now available via Wiley!
www.wiley.com/en-sg/Pallad...