Van wins IPMI Bright Futures Award Sponsored by Gero Family Trust

Huge congrats to G3 student Van Tran, who has been selected for the International Precious Metals Institute (IPMI) Bright Futures Award sponsored by the Gero Family Trust. The award recognizes Van’s research on the topic of palladium(II)-catalyzed C–C and C–heteroatom bond activation via β-X elimination. More information about IPMI and its student award programs can be found online at: https://www.ipmi.org/page/AwardPrograms. Way to go, Van!

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BT(S) Directing Group Preprint Online

In a pre-print appearing online today in ChemRxiv, Andrew, Kin, and Malkanthi describe the discovery and development of a benzothiazole sulfide, BT(S), directing group for use in catalytic alkene and C–H functionalization reactions catalyzed by palladium(II). The weakly coordinating nature of BT(S) makes it well-suited for reactions that rely on the directing group for selectivity control but also require conformational flexibility in key steps, such as the regioselective oxidative Heck arylation of 1,2-dialkylalkenes. The precursor compound, mercaptobenzothiazole is incredibly cheap (~$50/kg from MilliporeSigma), and the BT(S) can readily be converted to a BT sulfone for Julia olefination chemistry, among other transformations. Congrats to all of the authors, and thanks to Dr. Jason Chen from the Automated Synthesis Facility for guidance on Design of Experiment (DoE) optimization and kinetics runs. Click here for a link to the paper.

2019 Organometallics Class Kicks Off Today

The latest installment of the Scripps Research Organometallics Class (Chem 530) kicks off today! This class will be held on Mondays and Wednesdays, 10:00–11:30 AM, in the Keck Auditorium in the BCC building at Scripps. Like many Scripps courses, this class is open to anyone (in- or outside of Scripps) who is eager to learn more about this topic. If you are interested in attending and are not registered for the class, please contact keary@scripps.edu for more details. You can also follow along remotely! For the first time, all course materials, including video recording of lectures, will be freely available online: https://englelab.com/resources/

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Enantioselective anti-Carboboration of Alkenyl Amides – Now In Press

Over the past two years our lab and other labs around the world have been working hard to develop strategies for controlling enantioselectivity in palladium-catalyzed directed hydrofunctionalization and 1,2-difunctionalization reactions. Last month, we described a Pd(II)/chiral phosphoric acid system for enantioselective hydrofunctionalization with prochiral nucleophiles (click here). In a manuscript appearing online today in ACS Catalysis, we describe a new method for enantioselective anti-carboboration, representing the first time that a 1,2-difunctionalization within this family of reactions has been rendered enantioselectivity (click here). We also propose a new mechanistic model based on stoichiometric experiments to account for the stereoconvergent nature of the transformation. Congrats to all of the authors, Zhen, Xiaohan, and Tian (May). Special props to our two undergrad co-authors, Xiaohan and May! In case anyone missed it, a pre-print of this work was published on ChemRxiv back in early January (click here).

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Josh completes his undergrad internship

After a fun and productive six months in San Diego, Tianhua (Josh) Tang, finished his internship and now returns to Nankai University in Tianjin, China, to write his undergraduate thesis before graduating this spring. After earning his Bachelor’s degree, Josh will return to the US pursue his Ph.D. in organic chemistry (location TBD). During his time in the Engle lab, Josh worked under the mentorship of Mingyu and made significant contributions to the development of new catalytic alkyne functionalization methods. Outside of the lab, he enjoyed learning about American culture from his many friends in the lab and sampling the myriad restaurants in San Diego, including the various Chinese restaurants in Kearny Mesa.

Roman finishes his internship

The Engle lab bids farewell to our superstar visiting Master’s student Roman Kleinmans, who will now return to WWU Münster to pursue his Ph.D. studies with Prof. Frank Glorius. Roman was a valued member of Team Nickel, and made important contributions to advancing new methods for conjunctive alkene cross-coupling directed by simple functional groups. When he wasn’t in the lab, Roman learned how to surf, took a California road trip, and made many great friends in- and outside of Scripps. Props to Joe for great mentorship throughout Roman’s stay in San Diego. We will miss you, Roman! Best of luck in your Ph.D.