Mark Stradiotto

Meeting up with your big-time PhD advisor at a conference several years later…

Nickel‐Catalyzed P‐Arylation of HP(= O)(R/OR)2 Nucleophiles with (Hetero)Aryl Chlorides Enabled by DalPhos Ligation The development of broadly useful C-P cross-couplings of (hetero)aryl chlorides and HP(O)(R/OR)2 nucleophiles by use of nickel/DalPhos-based catalysts is described, along with findings from DFT studi....

Our collaboration w/ @markstradiotto.bsky.social and team is now out in Chem. Eur. J. (@chemistryeurope.bsky.social)!

Mark's team used DalPhos ligands for Ni-cat. C-P couplings, which we supported with DFT calculations of reductive elimination.

doi.org/10.1002/chem...

@cathweetman.bsky.social

a black and white photo of a man singing into a microphone with his mouth open . ALT: a black and white photo of a man singing into a microphone with his mouth open .

You were missed - and we could’ve commiserated over the loss of…

😂

It was a fantastic meeting! I learned so much, especially from Kevin 👆🏻!

Advances in Copper and Nickel C‐N and C‐O Cross‐Couplings of (Hetero)Aryl Chlorides Enabled by Ancillary Ligand Development The evolution of palladium-catalyzed C-N and C-O cross-coupling chemistry into first-choice methods for the synthesis of aniline and phenol derivatives can be attributed to innovations in ancillary l...

Checkout our new review on advances in Cu and Ni C-N and C-O cross-couplings of aryl chlorides enabled by ancillary ligand development. Such ligand advances offer promise as drop-in replacements for thermal Pd catalysis, without the need for new infrastructure. 😉

dx.doi.org/10.1002/chem....

Wayne would get mobbed and so what he would do in agreement for peace is sign a baseball - after each game they would do a draw and one of the players would get the game ball. Lucky me one day. 2/2

Coaching my son’s baseball team and was reminded of this little bit of memorabilia in my garage. As a kid I played AAA baseball (Guelph ON) against Brantford ON (vs Brent Gretzky - he humiliated us in both baseball and hockey) and his brother Wayne would show up to the games to watch him pitch. 1/2

The Devil Rides Again

My friend Adrian Raso’s new album is released today - lots of gypsy-jazz bangers! I did the original drum tracks for this album, but the label said “the drums sound like they are from Led Zeppelin” (a compliment 😂 ?) … the redone gypsy drumming sounds great! Enjoy!

open.spotify.com/album/30n4Nd...

You can tell they are really throwing it all out there when they start having Harper doing ads for PP. Not the endorsement they think it is 😂

@tsnofficial.bsky.social’s broadcast of the NCAA bball tournament is particularly entertaining when they broadcast the commentators during what must be commercial breaks in the US. Just learned about makeup preferences for covering up a bald head on television😂.

You get extra points for this one. I heard they especially have a focus on the metal recovery.😂

Nickel‐Catalyzed O‐Arylation of N‐Protected Amino Alcohols with (Hetero)aryl Chlorides The first effective base metal-catalyzed protocol for C−O cross-coupling of primary, secondary, and tertiary alcohol-containing N-Boc protected amino alcohols with (hetero)aryl chlorides, affording a....

Congrats to Kathleen, Emily, and Erika from our group for their recent report on challenging Ni-catalyzed O-arylation chemistry of pharmaceutical relevance 👍

chemistry-europe.onlinelibrary.wiley.com/doi/full/10....

Intercepting Ketone α-Arylation Intermediates in the DalPhos/Ni-Catalyzed Synthesis of Decorated Benzofurans and NH-Indoles Employing meso-PAd2-DalPhos (meso-L1) as an ancillary ligand, a single mechanistic landscape provides access to two thermal nickel-catalyzed transformations with broad scope commencing from α-(o-chlor...

A shout-out to Josh from my group, on his development of a single catalytic manifold for generating benzofurans or indoles selectively. A remarkable effort from a single trainee.👍

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

a man playing a guitar in front of a display of skulls with the word chaos on the bottom right ALT: a man playing a guitar in front of a display of skulls with the word chaos on the bottom right

Discussing Curtin-Hammett kinetics and all I think about is…

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/...

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 👍

Why one expert says it’s time to redefine cerebral palsy Focusing on early detection and prevention has skewed awareness of the permanent nature of the disability, a health expert writes.

Cerebral palsy should be reframed as “the most common lifelong physical disability,” instead of a childhood disorder, a professor of physical medicine and rehabilitation argues in a recent perspective article for the New England Journal of Medicine.

Yes please!

Throwing this out there…does anyone know how I can access the following…ideally in English translation?

Yagupol'skii J. Org. Chem. USSR 1986, 22, 1547-1554.

That bright red is 👍

Chem-peeps: Do any of you have experience using house N2 to run catalyst enabled gloveboxes? How is appropriate delivery pressure to fire the solenoids achieved, etc?

Bad idea? Good idea? 😂

Asymmetric Hydrogenation of Naphthalenes with Molybdenum Catalysts: Ligand Design Improves Chemoselectivity The asymmetric hydrogenation of substituted naphthalenes with a series of highly enantioenriched oxazoline imino(pyridine) (OIP) molybdenum cyclooctadiene precatalysts is described. The chemoselectivi...

A lovely ligand design paper from the Chirik group 👍

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

Why am I confident that the USA men’s basketball team will get third in the Olympics?

Because it is LeBronze.

(You’re welcome)

Study questions sustainability benefits of replacing palladium ... Common belief that Earth-abundant metals are green replacements for palladium may be misleading

Check out this recent article and my commentary in Chemistry World on Pd vs Ni and sustainability.

www.chemistryworld.com/news/study-q...

Post #1: Celebrating with newly minted Stradiotto group PhDs Kathleen and Nick on their graduation day!