SCF-ChemBio’s Post

I'm excited to share that our latest publication is now online in ACS Catalysis! This work presents our reaction design toward a general oxidative, cross-nucleophile alkene alkylarylation involving the chemoselective addition of two different boronic acids (alkyl and aryl) across vinylarenes. Under the reaction conditions with Mn(IV) as a potent oxidant, we successfully achieved a chemoselective 1-electron oxidation of alkylboronic acids over arylboronic acids while the latter favorably undergoes transmetalation with Cu(II) for the arylation step. One of the major challenges in this work was to carefully modulate various relative rates of elementary steps to suppress undesired side reactions but promote the alkylarylation reaction, selectively. This complementary method provides direct, modular access to a wide array of 1,1-diarylalkanes as prominent pharmacophores. I would like to thank my collaborators (Jianyang Yu, Alex Monterde , Sarah E. Tung, Ya-Nong Wang, PhD, Brittany Gay) and my PI, Prof. Kami L. Hull, as this work wouldn't be possible without their contributions!

Check out our new paper on oxidative, cross-nucleophile alkene alkylarylation between two different boronic acids (alkyl and aryl) across vinylarenes.

We are so happy that the second chapter of our exciting journey on the hydroelementation reactivity of SF5-alkynes and the value of TASP as a reagent has now been published in a peer-reviewed journal. We pre-published this work back in 2022 (https://lnkd.in/eYhhuDAK) after presenting our initial results on the synthesis of SF5 enamines from triisopropylsilylacetylene sulfur pentafluoride (or TASP) (https://lnkd.in/eeRqFbQF). While the hydroamination chemistry was recently published in Chemistry - A European Journal (https://lnkd.in/eCnzQuna), the hydrothiolation work has now been published in ChemPlusChem! (https://lnkd.in/eQQxFEng) This second report described for the first time the hydrothiolation of a SF5-substituted acetylene to give SF5 vinyl sulfides. We are pleased that this method proves to be robust, works under benchtop conditions, requires only short reaction times, shows excellent diastereoselectivity and yields up to 99% yield. Currently, there are difficulties with the accessibility of TASP, but we assure you that we will come back to this issue shortly! We also want to use the opportunity to highlight the soon after our first report released complementary work of Bizet on internal alkynes in ACIE in 2023 (https://lnkd.in/eXCWtuhS). See an overview of transition-metal-free hydroelementation reactions on SF5-alkynes in Figure 1 in our work. A next small step to make SF5 a functional group accessible to conventional laboratories!

Re-action! 👩🔬 I’m excited to share our latest publication on the effect of rhenium (Re) and chloride (Cl) promoters on silver (Ag) catalysts for ethylene epoxidation: https://lnkd.in/d8WuQrxV. In this study, we found that Re and Ag form a new crystalline phase (AgReO₄), even when introduced sequentially. Including the industrially vital Cl promoter, we show that changes in ethylene oxide selectivity relate to the catalysts' isomerization behavior. This means that the effects of Re and Cl are not limited to the selective oxidation pathway, but should also be considered for the subsequent isomerization reaction which influences the ethylene oxide selectivity. Many thanks to all co-authors who made this possible: Pim Weide, Kristiaan Helfferich, Justyna Zieciak, Marco de Ridder, Remco Dalebout, Tracy Lohr, John Lockemeyer, Peter van den Brink and Petra de Jongh. 

📢 Read our Review paper 📚 Amidoalkyl Naphthols as Important Bioactive Substances and Building Blocks: A Review on the Current Catalytic Mannich-Type Synthetic Approaches 🔗 https://lnkd.in/gT57SgYa 👨🔬 by Mr. Hristo Petkov and Prof. Dr. Svilen P. Simeonov #multicomponentreaction #Mannichreaction

Ritter's thianthrenium chemistry goes on (and on) with allenes. The study describes the convenient preparation of a bench stable allenyl thianthrenium salt which can be used in diverse manners which include Suzuki cross couplings but also as a 1,2-bis-electrophile. There is room for improvement, in particularly yieldwise. Nevertheless that's a new reagent to consider for allenylation. We will certainly do in regard of how thianthrenium salts have been successfully incorporated in our reaction toolkit at Spirochem. Congrats to the authors ! The open access article here: https://lnkd.in/ew6GQDqJ

The team Song Lin (Cornell University) published interesting articles in JACS that featured oxoammonium-catalyzed α-C−H oxidation of ethers to esters and N-substituted amines to amides. These both articles offer complementary reactivity and selectivity compared to commonly used radical-based methods, through a hydride transfer mechanism. https://lnkd.in/g26VJXez https://lnkd.in/gNaKE_qM

A chapter on one of the basic concepts of organic chemistry...

Check out our most recent publication on C3 selective hydroxylation of pyridines! As part of our collaboration with the Qin group at UTSW, we identified a highly atom-economic approach to access many medicinally relevant 3-hydroxypyridines through photo-induced isomerization of pyridine N-oxides. Big shout out 🎉 to Chen-Yan Cai, Rohan Merchant, Yuzuru Kanda and tian qin! #Merckchemistry #collaboration #synthesis

I'm ecstatic to share that our manuscript titled, "Diastereoselective [3 + 2] Cycloaddition between Tertiary Amine N‑Oxides and Substituted Alkenes to Access 7‑Azanorbornanes" was recently accepted into Organic Letters! I'd like to thank all of the contributing authors for their hard work on this project! Brief Description: We developed an efficient synthesis to access 43 novel nitrogen-containing heterocycles using commercially available or readily accessible starting materials. The core structure (7-azanorbornane) has demonstrated relevance as non-opioid pain relievers, dopamine transporters, glycosidase inhibitors, and possible anti-malarial treatments. You can read the full article free of charge at: https://lnkd.in/eVehQ8YH