Always Be Coupling

 Citation: Wellauer, J.; Pfund, B.; Becker, I.; Meyer, F.; Prescimone, A.; Wenger, O.S. Iron(III) Complexes with Luminescence Lifetimes of up to 100 ns to Enhance Upconversion and Photocatalysis. J. Am. Chem. Soc. ASAP.  https://doi.org/10.1021/jacs.4c18603 Summary Figure: Background: A good photocatalyst has a number of useful properties: 1. Absorb light at a wavelength that is easily accessible and does not interfere with other molecules. Ideally, this is visible light because most organic molecules do not absorb visible light (which is why everything is a white powder) and LEDs in visible light colors are easy to acquire.  2. Once the molecule has absorbed the energy in light, the catalyst needs to not immediately release that energy. Most molecules will absorb light, kick an electron up to the excited state, and then immediately relax back down and either release a different photon or wiggle their way back and release kinetic (heat) energy and be unproductive. If the ...

Citation: Tyler, J.L.; Trauner, D.; Glorius, F. Reaction development: a student's checklist.  Chem. Soc. Rev.  ASAP. https://pubs.rsc.org/en/content/articlelanding/2025/cs/d4cs01046a Summary Figure: Background: Finishing up this series on what goes into a method! Finally, I'll cover the scope and applications part of the paper, including my thoughts on what substrate scope should look like.  6. Scope (a) Is the substrate scope diverse? (b) Have you demonstrated functional group tolerance? (c) Have you defined the parameters of reactivity? I love the way they break this into 3 different questions. In general, I really like the way Frank Glorius approaches the subject of scope, and I am a fan of the robustness screen he developed.  I want to first tackle the question of functional group tolerance. There are a lot of different relevant functional groups. If you begin to include all the different heterocycles, it gets even more overwhelming. A quick list of (highly ...

Citation: Tyler, J.L.; Trauner, D.; Glorius, F. Reaction development: a student's checklist.  Chem. Soc. Rev.  ASAP. https://pubs.rsc.org/en/content/articlelanding/2025/cs/d4cs01046a Summary Figure: Background: Continuing to go through this "checklist" about how to turn a discovered reaction into a paper. Today's section will focus on how to identify interesting mechanistic features of the reaction, which covers parts of steps 2, 3, and 5 on their checklist: 2. Kinetics and Thermodynamics (a) Can the rate law be determined? In most cases, kinetic data is not collected for a given reaction because it is moderately difficult and gives fairly specific information. The authors make a good point that collecting rate data could give highly valuable information about stoichiometry that can inform optimization of the reaction. If you have a reaction that is first order with respect to a given additive (say, a halide salt), then you can increase the quantity of that additive t...

 Citation: Tyler, J.L.; Trauner, D.; Glorius, F. Reaction development: a student's checklist. Chem. Soc. Rev. ASAP. https://pubs.rsc.org/en/content/articlelanding/2025/cs/d4cs01046a Summary Figure: Background: This is a bit of a weird one today. I was recently shown this paper from the minds of Trauner and Glorius, which they describe as "a helpful guide for synthesis development, allowing you to thoroughly investigate the chemistry in question while ensuring that no key aspect of the project is overlooked." Now, Trauner and Glorius have developed a lot more reactions than me, but this checklist confuses me, because it skips a lot of the steps and seems very out of order. I think it's worth looking at (a) what points they make and (b) how to actually go about doing what they prescribe.  How it works: The paper is broken down into 8 sections, which I have copied below: 0. How to discover a reaction (a) develop it from the older literature.  (b) accidentally (c) by ana...

 Citation: Skotnitzki, J; Kremsmair, A.; Keefer, D.; Gong, Y.; de Vivie-Riedle, R.; Knochel, P. Stereoselective Csp3-Csp2 Cross-Couplings of Chiral Secondary Alkylzinc Reagents with Alkenyl and Aryl Halides. Angew. Chem. Int. Ed. 2019   59 , 1, 320-324.  Summary Figure: Background:  In general, for an asymmetric Csp2-Csp3 cross-coupling reaction, there are 2 ways to set the stereochemistry.  The first method is to ablate the existing stereocenter on the sp3 coupling partner, usually by forming an alkyl radical (although not always), and then use a chiral ligand to form a chiral alkyl-metal species.  The second method is to use existing stereochemistry of the sp3 coupling partner and activate it with stereospecific elementary steps, usually oxidative addition. Famously, the Tsuji Trost reaction proceeds through an SN2-like oxidative addition, which inverts the stereochemistry at the electrophile: ( note how the X was on the dash, and the Pd is now on the wed...