Zhen is selected as a finalist for the 2019 Reaxys PhD Prize

Congratulations to Zhen, who has been selected as a Finalist for the 2019 Reaxys PhD Prize! Zhen was acknowledged for his 2016 J. Am. Chem. Soc. publication, “β,γ-Vicinal Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Directed Nucleopalladation.” The 45 Finalists, selected from 360 nominations, are invited to a the Reaxys PhD Prize Symposium, which takes place in Amsterdam on Oct 3 and 4, 2019.

(BT)S Directing Group paper accepted for publication

For the past four years, a major focus of our research has been developing substrate-directed Heck- and Wacker-type alkene hydrofunctionalization and 1,2-difunctionalization reactions. In particular, we’ve previously found that alkenyl amides containing removable bi- and tridentate directing groups are highly effective substrates, owing to the ability of the directing group to facilitate regioselective addition of the first reaction partner and then subsequently form a stabilized palladacycle that can be intercepted with a proton, nucleophile, or electrophile. Based on these results, we became interested in identifying news weakly coordinating directing groups that can enable regioselective addition of a nucleophile and then allow a site-selective β-H elimination.

In a manuscript appearing online today in ACS Catalysis, we describe the discovery and development of the benzothiazole thioether, (BT)S, directing group for oxidative Heck and C–H activation reactions (click here). In a colossal 15-page-long (!!!) paper covering reaction development, mechanistic studies, and applications in total synthesis, Andrew, Kin, and Malkanthi, demonstrate the unique coordination properties of (BT)S and showcase its synthetic versatility . Congrats to the three Engle lab authors listed above, and huge thanks to our tireless collaborator Jason from the Scripps Research Automated Synthesis Facility for guidance on high-throughput experimentation, design of experiments, and kinetics! In case anyone missed it, a pre-print of this work was published on ChemRxiv back in early April (click here).

Welcome Houxian and Zhongqian!

Two senior undergraduates from Tsinghua University, Houxian and Zhongqian, started their internships with Zhen and Yang, respectively. They’re already doing great work using the glove box and running reactions. Summer time in the Engle lab is going to be a blast.