Matthew V. Joannou

I do miss it sometimes 😊

Ah yes, the elusive oxygen isotope 178-O, can only be found at a rest stop halfway between Istanbul and Kuşadası in Susurluk, Turkiye 🤓 amazing panini sold there as well #realtimechem #isotopes #goturkiye

GC with helium as the carrier gas, GC-MS in single ion mode to detect for water only, IR (but not sure how low the detection limit is). Or, NMR the solvent with a sealed insert of C6D6 and TpyNiMe and see if you see methane. If I could send you a KF...I would, it's the best 🤓 good luck!

Advancing Base Metal Catalysis: Development and Execution of a Ni-catalyzed Borylation/Pd-catalyzed Suzuki Telescoped Process The development and execution of a nickel-catalyzed borylation/palladium-catalyzed Suzuki telescoped process utilizing the inexpensive NiCl2·6H2O precatalyst for the borylation step are reported. The ...

I see a pattern here...happy to share another story about advancing Base Metal Catalysis on scale! This time, a Ni-Borylation followed by a Pd-Suzuki coupling, Ni and Pd can definitely be friends 😊 Congrats to all the co-authors! #BMSChemistry pubs.acs.org/doi/10.1021/...

Development of an Inherently Safe and Scalable Nickel-Catalyzed Borylation Process of an Aryl Sulfamate A safe and scalable synthesis of A, a key aryl boronate ester intermediate toward an immunology asset udifitimod, via a Ni-catalyzed Miyaura borylation is reported. High-throughput experimentation, design of experiment, and reagent stability/compatibility studies were used to optimize the reaction conditions and furnish the borylation of aryl sulfamate B in 80–85% yield and >98% purity/potency. Significant hydrogen off-gassing was observed during the reaction, metal remediation, and crystallization steps of the first-generation process, and efforts were made to quantify, understand, and mitigate this off-gassing to ensure a safe and reliable scale-up. Two multikilogram batches of the process were successfully run to afford A in an average 85% yield, >99% potency, and ≤28 ppm residual Ni. Using the mechanistic learnings from this work, a second-generation process was developed which significantly reduced hydrogen off-gassing at all steps of the process, as well as increasing final yield and reducing process mass intensity. This second-generation process was demonstrated on a 1 kg scale to afford the product in 90% yield, >99% purity/potency, and 50 ppm residual Ni.

So excited to share our work on learning more about EAM catalysis on scale! Featuring two of our favorites: nickel and boron 🤓 Who knew there were so many ways to make hydrogen in a borylation reaction 🤪 Congrats to all the co-authors! #BMSChemistry pubs.acs.org/doi/10.1021/...

I'm colorblind so it took me a while to find this place. Anything good here? 😊