Tungsten-Catalyzed Stereodivergent Olefin Isomierzation – Paper Now In Press

The final peer-reviewed version of our tungsten-catalyzed olefin isomerization method appears in press this week in Chemical Science. The method offers a mild and reliable way to perform kinetic isomerization of β,γ-unsaturated carbonyl compounds without competitive formation of the thermodynamic (conjugated) byproduct. We find that E versus Z stereoselectivity can be controlled by modulating the ligand environment around the tungsten center to grant access to either isomer as desired. Congrats to the project team, Tanner, Camille, Hang Chi (Calvin), and Raul!

For a link to the paper in Chemical Science, click here: https://pubs.rsc.org/en/content/articlelanding/2024/sc/d4sc07093c

As a reminder, an earlier version of this paper was published as a pre-print in ChemRxiv in November 2023: https://chemrxiv.org/engage/chemrxiv/article-details/6554cf6adbd7c8b54b514d16

Omar passes his viva

Congrats to Skaggs Oxford Scholar and Engle lab member, Omar Apolinar, who successfully passed his viva (thesis defense) at Oxford to complete his program, simultaneously earning a Ph.D. in Chemistry from Scripps Research and a D.Phil. in Biochemistry from the University of Oxford. In the Engle’s lab, Omar expanded the scope of native directing groups in nickel-catalyzed olefin diarylation and developed the first enantioselective three-component diarylation of unactivated terminal and internal olefins. At Oxford, Omar performed research under the joint mentorship of Profs. Simon Aldridge and Véronique Gouverneur, developing novel Ca–F complex for nucleophilic fluoride delivery. Congrats Dr. Dr. Apolinar!

Alkyl Sulfonyl Fluorides are Untapped Ambiphiles in Catalysis – New Pre-Print Online

Together with the Sharpless, Blackmond, and Liu labs, as well as the teams at Enamine and Pfizer, in a ChemRxiv pre-print this week, we explore a family of intriguing chemicals with largely unannotated reactivity, alkyl sulfonyl fluorides. Under PdII/PdIV catalysis, we unlock the ambiphilic reactivity of alkyl l sulfonyl fluorides with olefins to access unique substituted cyclopropanes.

This was a fun collaboration spanning many years made possible a by a great team, including Yilin Cao, Warabhorn (Por) Rodphon, Turki Alturaifi, Al Vicente Riano Lisboa, Hermione Ren, Job Struijs, Hui-Qi Ni, and several industrial collaborators. Congrats!

For a link to the ChemRxiv pre-print, click here: https://chemrxiv.org/engage/chemrxiv/article-details/672b9b3cf9980725cf547804

Job completes his stint as a visiting student

After several months working jointly between the Engle, Blackmond, and Baran labs on organonickel catalysis, Job Struijs wraps up his time at Scripps Research. Job made a huge impact during a short time bringing a mechanistic perspective to numerous different projects. Job will now return to Oxford to complete his D.Phil. with Profs. Veronique Gouverneur and Simon Aldridge. Thanks for all of your hard work, Job!

Camille Successfully Defends Her Thesis

Congrats to Dr. Camille Rubel who (in the words of Donna Blackmond) gave a “scary good” thesis defense to kickstart Halloween. Camille’s thesis research spanned electrochemistry to methods development and took her from San Diego, CA, to Lyon, France, and back. Congrats on a stellar body or work, Dr. Rubel!

Engle Lab Pumpking Carving

As per annual tradition, the Engle lab gathered to show off our pumpkin carving skills, eat tasty food, and enjoy the fall weather in San Diego. We welcomed friends, family, and lab alumni from near and far for a fun afternoon of Halloween-themed festivities.

Collaborative study on molecular glues now online as pre-print

We joined forces with the lab of Prof. Michael Erb, star postdoc Dr. Jamie Schaum, and a team of chemical biologists in and outside of Scripps Research on a study detailing how to leverage high-throughput chemistry to convert existing ligands for proteins of interest into molecular glues. In this study, we were able to put our new pre-catalyst, Pd(COD)(DQ), to good use in a challenging C–N coupling reaction. Congrats to all of the co-authors on a great collaborative study!

For a link to the pre-print in BioRxiv, click here: https://www.biorxiv.org/content/10.1101/2024.09.30.615685v1

Evan joins the lab as a postbac

After completing his undergrad degree at Columbia University, San Diego native Evan Morgan joins as the Engle lab’s newest member. At Columbia, Evan gained a diverse set of research experiences in geochemistry and organic chemistry with Profs. Benjamin Bostick and Tom Rovis. In the Engle lab, Evan will pursue research in organometallic catalysis for a year before graduate school. Welcome Evan!

Air-stable catalytic copper-hydride cluster – Pre-print available online

Together with the labs of Rodolphe Jazzar (UCSD/CNRS) and Pierre-Adrien Payard (Université Claude Bernard Lyon), this week we report a bench-stable CuH cluster inspired by Stryker’s reagent.

Multicenter-2-electron bonds play a pivotal role in templating cluster assembly during synthesis, allowing incorporation of the CAAC ligand. The pronounced stability of the cluster arises from attenuated hydride mobility, as probed by experiment and theory. This great team effort spanned three institutions and was led by Quentin (Lyon), Skyler Mendoza (Scripps Research), and Jesse Peltier (UCSD).

For a link to pre-print on ChemRxiv, click here: https://chemrxiv.org/engage/chemrxiv/article-details/66c3a7fd20ac769e5f193252