Congrats to the Class of 2020!

Huge congratulations to the Class of 2020! The Engle lab is incredibly proud of our recent, PhD, visiting PhD, and college students who are moving on to incredible jobs, postdocs, and graduate programs around the world!

Graduate Students (PhD)

Dr. Joseph Derosa: Caltech (Postdoc, J. Peters)

Visiting Graduate Students (PhD)

Dr. Xin Wang (Nankai University Medical School)

Undergrads/Visiting Undergrads

Jiahao Chen (Fudan U): Fudan University (Ph.D. in Chemistry)
Ryan Helsel (UCSD): UCSB (M.A. in Chemistry / Teacher Education)
Hou-Xiang Lu (Tsinghua U): Tsinghua University (Ph.D. in Chemistry)
Tian-Zhang Qiao (Nankai U): Cornell U (Ph.D. in Chemistry)
Zi-Yang (Nick) Qin (USTC): Caltech (Ph.D. in Chemistry)
Juntao Sun (Nankai U): Scripps Research (Ph.D. in Chemistry)
Zhong-Qian Wu (Tsinghua U): UChicago (Ph.D. in Chemistry)

We are also excited that two 2019 graduates will be pursuing their Ph.D. degrees next year:

Hanh Ngyuen (UCSD): UC Irvine (Ph.D. in Chemistry)
Tim Gallagher (Claremont McKenna): Scripps Research (Ph.D. in Chemistry)

1,1-diborylation pre-print online

Appearing today in a pre-print on ChemRxiv, Yang and Zhong-Qiang describe a copper-catalyzed tandem process for preparing differentially protected E-configured 1,1-diboryl alkenes from terminal alkynes. Mechanistically the reaction proceeds through the intermediacy of an alkynyl–Bdan intermediate which undergoes in situ hydroboration. Special congrats to undergrad co-author, Zhong-Qian, who is headed to UChicago to start his Ph.D.

For a link to the pre-print, click here: https://chemrxiv.org/articles/Synthesis_of_Stereodefined_1_1-Diborylalkenes_via_Copper-Catalyzed_Diboration_of_Terminal_Alkynes/12133404

directed cyclization pre-print online

Appearing today as a pre-print in ChemRxiv we describe a series of Pd(II)-catalyzed intramolecular alkene hydrofunctionalization reactions, where we take advantage of a proximal directing group to recruit the metal catalyst and promote otherwise disfavored rings closures. This work was part of a fun collaboration with the Liu group at the University of Pittsburgh and the Xiang group at Nankai University Medical School. Congrats to the three project leads: Xin (a visiting PhD student from Nankai University who spent one year in our lab in La Jolla, Zi-Qi (a second-year PhD student at Scripps Research), and Binh (a postdoc at the University of Pittsburgh). Props to the rest of the team, especially former high-school intern Jessica Xu, who carried out critical proof-of-concept studies in the summer of 2016 and is now an undergraduate student at MIT. Way to go, team!

For a link to the pre-print, click here: https://chemrxiv.org/articles/Controlling_Cyclization_Pathways_in_Palladium_II_-Catalyzed_Intramolecular_Alkene_Hydrofunctionalization_via_Substrate_Directivity/12090402

Keary selected as 2020 ONR Young Investigator

The Engle lab is excited and honored to be selected for the 2020 Office of Naval Research Young Investigator program. This award through the Advanced Energetic Materials program will support a project titled, “Selective Alkene Functionalization as a Platform for Energetic Materials Development“. We are looking forward to applying our experience in catalytic alkene functionalization to streamline the discovery and development of new energetics — should be a blast 😉

For a full list of 2020 awardees, click here: https://www.onr.navy.mil/Education-Outreach/Sponsored-Research/YIP/2020-young-investigators

Alena wins a 2020 NSF Graduate Research Fellowship

Huge congratulations to G2 student Alena Vasquez who has been selected for a highly competitive 2020 NSF Graduate Research Fellowship. In the Engle lab, Alena has developed an α-selective reductive Heck hydroarylation of acrylamides and acrylates, which was recently described in ChemRxiv. Outside of the lab, Alena volunteers as a refugee tutor, runs workshops for younger students through the Bario Logan College Institute, and serves as the Engle Lab’s Outreach coordinator, among other activities. She is also an animal enthusiast who loves spending time with her pet cats. We are so proud of you, Alena!

For a full link of awardees, click here: https://www.research.gov/grfp/AwardeeList.do?method=loadAwardeeList

Chiral Transient Directing Group Paper – Now In Press

During the past five years, our lab and others have demonstrated the power of directing auxiliaries in catalytic alkene functionalization. While highly enabling in their own right, these auxiliaries require additional steps for installation and removal, which detracts from their practical utility. In an effort to overcome this issue, we are excited to disclose the first successful demonstration of co-catalytic “transient” directing groups in asymmetric Heck-type migratory insertion in a paper that appears today in Angewandte Chemie International Edition. Under simple reaction conditions, a commercially available amino acid is able to reversibly condense with an aldehyde on the substrate and guide aryl addition to the β-position of the styrene-type substrate. Congrats to Luke, Zi-Qi, Van, and Ruohan from our lab; and our computational collaborator Tuğçe from the Liu Lab at the University of Pittsburgh. In case anyone missed it, a pre-print of this work was deposited in ChemRxiv back in September (click here).

For a link to the paper, see: https://onlinelibrary.wiley.com/doi/10.1002/anie.202001069

Alpha-Hydroarylation pre-print is online

The group’s latest collaboration with Bristol-Myers Squibb describing a palladium(0)-catalyzed α-selective hydroarylation of acrylates and acrylamides is now online at ChemRxiv. The method achieves this unusual mode of regioselectivity via the intermediacy of a PdII(Ar)(H) intermediate, as supported by kinetics, in situ 31P NMR, and other experiments. The utility of the method is underscored by the fact that it can be run in an open-flask fashion, can employ water as a cosolvent, and can tolerate a variety of heterocycles and base-sensitive functional groups. Congrats to Alena and John from the Engle lab, and Candice and Emily from BMS!

For a link to the pre-print, click here: https://chemrxiv.org/articles/Catalytic_-Hydroarylation_of_Acrylates_and_Acrylamides_via_an_Interrupted_Hydro-Dehalogenation_Reaction/12003444