Posts | Nick Chiappini (@ndchiappini@mastodon.online)

Nick Chiappini

@ndchiappini@mastodon.online

Lover of weird rxns, reactive intermediates, and equitable sci. Asst Prof at UNCW via Stanford (Du Bois) and Princeton (Knowles). He/him; queer af
#chemistry

November 4, 2022

23 Posts 188 Following 266 Followers

Posts Posts & Replies Media

-40 being the same in Celsius and Fahrenheit is one of those things that FEELS absolutely incorrect but is actually correct

Really friggin excellent work from Liam Ball's group on bringing meta-arylation of phenols to the realm of possibility for Bi(V)

Ball consistently wows me with the scale of some of his group's preps (16 g of the divergent bismacycle!!)

https://www.nature.com/articles/s41557-022-01101-0

Nature

meta-Selective C–H arylation of phenols via regiodiversion of electrophilic aromatic substitution - Nature Chemistry

The strong regiochemical preferences of electrophilic aromatic substitution have played a key role in defining the diversity of accessible chemical space. Now, it has been shown that the electrophilic arylation of phenols can be achieved at the electronically disfavoured meta-position via a formal 1,2-migration of a key σ-complex intermediate.

And also for the stoichiometric skeptics out there, recovery of the bismacycle is really straightforward. Basically run your column and then flush with polar solvent and a bit of acetic acid and you get the bismacycle back intact (from their previous work with these)