Facile Solid-State Decomposition of Sodium Alkoxide Salts – Pre-Print Now Online

NaOMe, NaOEt, and related bases are widely used in organic synthesis and are readily available in solid form as free-flowing white (or off-white) solids. During research into cross-coupling reactions, our lab in collaboration with Bristol Myers Squibb discovered that these bases undergo rapid decomposition under air through a complex sequence of events. Today we disclose a pre-print in ChemRxiv describing our efforts to understand this phenomenon. It turns out that this process is so pervasive that even “new” commercial lots of these bases can contain almost none of the desired material. This was a long and circuitous detective story that challenged us to use every analytical trick in the book, from Karl Fischer titration to solid state 23Na NMR.

Read the full story here: https://chemrxiv.org/articles/preprint/An_Under-Appreciated_Source_of_Reproducibility_Issues_in_Cross-Coupling_Solid-State_Decomposition_of_Primary_Sodium_Alkoxides_in_Air/12818234

BCB Hydroboration Pre-Print Online

The latest story from our ongoing collaboration with the Liu group at the University of Pittsburg and Pfizer, Inc. appears online today in pre-print form on ChemRxiv. The new method effect hydroboration of benzylidenecyclopropanes, -azetidines, -oxetanes, and other related substrates. Key to the success of the reaction was the discovery of a specially modified dppbz ligand for the copper catalyst, which promotes the reaction through T-shaped π-stacking and other non-covalent interactions with the substrate. Congrats to G3 student Taeho and our high-school intern Kane from the Engle lab, Tuğçe from the Liu lab, and Gary, Alex, Sajiv, Ryan, Ru and Indra from Pfizer!

Please click here for a link to the pre-print: https://chemrxiv.org/articles/preprint/Multifaceted_Substrate_Ligand_Interactions_Promote_the_Copper-Catalyzed_Hydroboration_of_Benzylidenecyclobutanes_and_Related_Compounds/12788390

2nd-Year Students Pass Qual Exams with Flying Colors

Congratulations to our Engle lab’s G2 students (Class of 2023), Taeho Kang, Zi-Qi Li, Luke Oxtoby, and Alena Vasquez, for passing their qual exams and advancing to candidacy. Despite the COVID-19 pandemic, lab shutdown, and challenging working circumstances, these four maintained a great attitude and mastered the art of giving a great scientific talk over zoom. Looking forward to seeing what this class has in store for the next three years!

2020 OM Bootcamp kicks off this week!

The 2020 Organometallics Bootcamp kicks off this week (Mon, 8 am PT), and for the first time it will be held entirely over zoom. We are opening it up to any interested undergraduate students (especially those from PUIs!) who may have missed out on summer research opportunities. Please email keary(at)scripps.edu for more info if you are interested in learning more and potentially participating. Hope to see you there!