Directed Alkene Carboboration and -Silylation Paper – Now Accepted

The latest work from our collaboration with Bristol-Myers Squibb was recently accepted for publication in Angewandte Chemie International Edition. This manuscript described the developments of new methods for Pd(0)-catalyzed alkene 1,2-carboboration and -silylation. Compared to prior art, these methods are much more effective with internal alkenes (including tri- and tetrasubstitued). We even show examples of dearomative 1,2-carboboration of electron-rich heterocycles. Lastly, we identified a chiral directing group that enables control of the absolute configuration of the final products. Congrats to all Engle lab coauthors, Zhen, Hou-Xiang, Jiahao, Xiaohan, and Yang, especially our three undergrad co-authors, Hou-Xiang, Jiaohao, and Xiaohan (now in the Ph.D. program at UCSB). It was awesome teaming up with BMS again for this project — thanks to Ryan and Matt for an awesome collaboration!

For a link to the paper, click here: https://onlinelibrary.wiley.com/doi/10.1002/anie.201910304

Chiral Transient Directing Group Preprint Online

We are excited to share a project many years in the making. For the first time, we have succeeded in using chiral transient directing groups to enhance reactivity, control regioselectivity, and achieve stereoinduction in an intermolecular reductive Heck hydroarylation of alkenes. This transient directing group strategy obviates the directing group installation and removal steps that are common in directed alkene functionalization, representing a positive step forward in efficiency and sustainability. Congrats to all of the Engle lab authors, Luke, Zi-Qi, Van, and Ruohan, as well as our collaborators Tuğçe and Peng from the Liu lab. For a link to the pre-print, click below:

https://chemrxiv.org/articles/A_Transient_Directing_Group_Strategy_Enables_Enantioselective_Reductive_Heck_Hydroarylation_of_Alkenes/9795338

Alkene 1,2-Carboboration Review Accepted for Publication

Our lab had the honor and privilege to contribute to a special issue of the Israel Journal of Chemistry honoring 2019 Wolf Prize Awardees and catalysis legends, Professors Stephen L. Buchwald and John F. Hartwig. In this review, Zhen, Yang, and May teamed up to provide an overview of recent developments in alkene 1,2-carboboration using different transition metal catalysts. This is a fast-moving field, so it’s hard to keep up with all of the exciting developments, but hopefully this review will be a good place to start. For a link to the paper, click here.

Conjunctive Cross-Coupling with Allyl Groups – Pre-print Online

In a pre-print appearing online today in ChemRxiv, Van, Zi-Qi, Tim, and Joe describe the first successful integration of allyl electrophiles into nickel-catalyzed conjunctive cross-coupling. Key to the success of this reaction is use of a series of weakly coordinating heterocycle directing groups that allow the alkene moiety of the allyl group to coordinate and promote challenging C(sp3)–C(sp3) reductive elimination, as supported by computational studies in collaboration with the Liu group at the University of Pittsburgh. Click here for a link to the paper.

Fourth Annual Beach Day!

The Engle Lab took a break from lab work to celebrate the arrival of three new graduate students, the successful PhD defense by Zhen, and everyone’s hard work over the past year. We stuck to tradition and grilled food, played volleyball, and relaxed!

Zhen defends his PhD!

Today, we celebrated Zhen passing his thesis defense with flying colors! It’s been a honor to work with him these past few years and we will be forever grateful for the leadership he showed this lab! He will soon be off to post-doc with Professor Frances Arnold at Caltech!