Welcome Yilin!

We have a new undergraduate intern Yilin, from UCSB. She has explored nickel-catalysis in aqueous micellar conditions as an undergraduate research assistant in Prof. Lipshutz’s group, and now she will be expanding her experience in nicekl catalysis, joining the Team Nickel under the mentorship of Ziqi.

Cross-metathesis route to alkenyl AQ amides

Over the years we’ve experienced first-hand the frustrations of resorting to circuitous synthetic routes to access substituted alkenyl AQ amide substrates, which serve as cornerstones of AQ-directed alkene functionalization chemistry. To address this Hui-Qi, Zi-Qi, and Van teamed up to develop a concise and modular method using cross-metathesis with the Grubbs 2nd generation catalyst. Remarkably the catalyst is impervious to the AQ group, allowing direct coupling of terminal alkenyl AQ amides with a variety of terminal alkenes. In one case, we shorten a four-step sequence to a single high-yielding step. This paper is part of a special issue in Tetrahedron celebrating Prof. Guangbin Dong’s 2021 Tetrahedron Young Investigator Award. Well done team!

For a link to the paper, click here: https://www.sciencedirect.com/science/article/abs/pii/S0040402021005019

Welcome José!

We have a summer visiting gradudate student José González from Gulías group at CIQUS-USC, Spain. He has been working on enantioselective Pd-catalyzed C-H activation at Gulías group. In the Engle lab, he is turning his attention to Ni-catalysis, collaborating with Taeho.

Andrew Successfully Defends his Thesis and Departs for BCG

On a whirlwind of a day, Andrew successfully defended his thesis over Zoom, dropped by campus for his champagne toast, and then hit the road for the transcontinental drive back to his hometown of Philadelphia. Starting next week, Andrew will begin his career as a consultant at Boston Consulting Group. We’re so grateful for your many contributions to the lab and proud of your accomplishments, Andrew. Good luck on this next adventure!

Enantioselective 1,2-Arylfluorination of Alkenes using a Transient Directing Group Strategy – Paper Now in Press

The final version of our manuscript describing the palladium-catlayzed enantioselective 1,2-arylfluorination of alkenes using a transient directing group (TDG) strategy is online today in J. Am. Chem. Soc. In the study we apply Design of Experiments (DoE) to optimize this challenging three-component coupling of alkenes, arylboronic acids, and [F+] electrophiles, which helps to account for the complex interactions between variables in this system. We further elucidate the reaction mechanism using reaction progress kinetic analysis (RPKA). In terms of preparative applications, the method proceeds in high ee and d.r., allowing formation of full substituted C(sp3)–Ar and C(sp3)–F centers. The transformation is the first time that 1,2-difunctionalization has been achieved using a TDG approach and as such represents an important milestone for our lab and for the field. Hats off to Zhonglin, Luke, Mingyu, Zi-Qi, Van, and Yang!

For a link to the paper, click here: https://pubs.acs.org/doi/10.1021/jacs.1c03178

The work first appeared on ChemRxiv back in January. Check out the pre-print here: https://chemrxiv.org/articles/preprint/A_Transient_Directing_Group_Strategy_Enables_Enantioselective_Multicomponent_Organofluorine_Synthesis/13537283

Van departs for Gilead

With the lab fully vaccinated we were very happy to be able to give Dr. Van Tran a proper send off, including a Korean BBQ trip and a champagne toast. Best of luck in your next adventure as a process chemist at Gilead, Van! We miss you already.