After a two-month stay in the Engle lab, Tian-Zhang departs San Diego today to return to Nankai University just in time to begin his junior year. Tian-Zhang deepened his knowledge of organometallic chemistry and catalysis, made many new friends, and had the opportunity to explore several fun locations up and down the West Coast. Thanks to De-Wei for great mentorship throughout the summer!
After a brief lab cleanup, the Engle group made the short trip up to the Del Mar Beach, for an afternoon of grilling, swimming, cards, volleyball, and relaxing. It was a great opportunity to celebrate the arrival of several new group members and the departure of Tian-Zhang, who completes his two-month internship next month. Thanks to the social team for organizing a great day!
Tianhua (Josh) UG4 started his 6 month internship working with Mingyu G3 and has already began making some chiral phosphine ligands. Josh is excited to learn about catalysis and trying In-n-out burger.
Roman M2 begins his visiting masters program from the Glorius Lab. Roman is looking forward to enjoying the last bit of summer here in San Diego and going to the beach.
Our collaboration with Pfizer describing a γ-selective hydroarylation of alkenyl carbonyl compounds using arylboronic acid coupling partners was accepted for publication today in Chem. Sci. (click here). With this discovery for the first time we are able to use ubiquitous aryl boronic acids to install essentially any aryl group at will as the nucleophilic component in catalytic directed alkene 1,2-functionalization. Though the reaction mechanism was not a major focus at the time of our initial submission, we were encouraged by reviewers to think more about the details of this system (particularly our preliminary deuterium-incorporation experiments), and this ended up leading us along a fruitful line of inquiry that included Reaction Progress Kinetic Analysis (RPKA). This was an awesome team effort that involved critical contributions from members of our lab (Rei, Tanner, Kin, and Rohan), the Blackmond lab (David), and Pfizer (Gary, Shouliang, Mingying, Fen, and Indra). Special kudos to our high school co-author Rohan from High Tech High International, who was an intern in the lab earlier this year. In case anyone missed it, a pre-print of this work was published on ChemRxiv back in April (click here).
Congratulations to G4 student Joseph Derosa, who has been selected for the prestigious 2018/2019 Turner B. and Lesly Shelton award from the Skaggs Graduate School at Scripps Research. Well done and well deserved, Joe!
About the award: Mrs. Lesly Starr Shelton was among the most ardent supporters of Scripps Research. Mrs. Shelton, alongside her husband Turner, supported both undergraduate and graduate education at several insitutions across the US, but Scripps Research was perhaps closest aligned with her personal passions. Mrs. Shelton’s family had been involved in the early pharmaceutical industry and she knew firsthand the value of education in basic research and its application towards the diagnosis, prevention and treatment of disease. The Skaggs Graduate Schools continues to honor Mrs. Shelton’s legacy and passion for education and research each year by awarding the Turner B. and Lesly Shelton Scholarship to a promising young scientist at Scripps Research.
Congrats to rising G3 student Andrew Romine for successfully passing his qualifying exam and advancing to candidacy. Andrew know how to celebrate in style—all while donning proper PPE! Well don and keep up the great work, Andrew!
Four new first year students start their research in the Engle Lab: Lucas Oxtoby (UW Madison), Taeho Kang (KAIST), Zi-Qi Li (Nanakai University), and Alena Vasquez (Oregon State). They have already put in a month of hard work before classes start next week, and we are excited to have them as part of the team!
Our paper describing a reductive Heck hydroarylation reaction that is compatible with a variety of terminal and internal alkenes was accepted for publication today in ACS Catal. (click here). To bring this reaction to fruition we employ a high ligand-to-Pd(0) ratio to maintain coordinative saturation around the metal and prevent beta-hydride elimination. We originally focused the study exclusively on terminal alkenes but discovered that the reaction is actually reasonably efficient with cyclic internal alkenes during the peer review, so thanks to the referees for suggesting those experiments! (Acyclic internals are still a work in progress.) One of the most notable attributes of the reaction is that is extremely simple to set up, as it uses reagents that are commonly available in any organic chemistry lab and can be performed without exclusion of air or moisture. As a bonus, it tolerates a variety of Lewis basic functional groups, including pyridine heterocycles. Hats off to John who was the mastermind behind this project and performed 100% of the experiments in the final publication. As a reminder, a pre-print of this work was published on ChemRxiv back in June (click here).
Congratulations to G4 student Zhen Liu who has been selected as the recipient of the 2017–2018 Lesly Starr Shelton Award for Excellence in Chemistry Graduate Studies. Way to go, Zhen!
About the award: Lesly Starr Shelton was a generous benefactor who has provided in her estate for an endowed scholarship in the chemistry graduate program at Scripps Research. Ms. Shelton has supported a student through this award since 1997, and was deeply interested in encouraging students in the sciences throughout her life.
In a paper appearing today online in Nat. Chem., the Engle lab reports a method of cleaving typically unreactive carbon–carbon and carbon–heteroatom bonds via β-X elimination from alkylpalladium(II) intermediates. This reaction enables functional group metathesis (or exchange) between C(sp3)–C, C(sp3)–N, C(sp3)–O, and C(sp3)–S, and C(sp3)–F bonds, which has enabled the development of synthetically useful new transformations, such as the upgrading of inexpensive natural amino acids to valuable non-natural counterparts. Congrats to the project team of Van, John, and Kin on this awesome piece of work. Click here for a link.
(not pictured: Kin)
Molecular Complexity through Catalysis 