It’s that time of year again🥳! This year, we were able to hold our traditional Engle group holiday party in-person. We shared delicious food, exchanged gifts through a white elephant game (fun!), and enjoyed the nice chilly December weather of San Diego. Tints of red and green color piqued our holiday excitement. From our lab to yours, we wish everyone a joyous holiday season and a most prosperous and healthy New Year!
Diamines are a family of valuable compounds with diverse functions. In many cases, they are not trivial to prepare, particularly when the two nitrogen atoms contain different substituents. In a new study that appears this week on ChemRxiv, our lab in collaboration with scientists from Bristol Myers Squibb (BMS) developed a reaction where a free amine can direct regioselective 1,2-carboamination of an unactivated alkene, representing the first time that an unprotected amine has been used to direct three-component alkene difunctionalization. Key to the successful development of this method was judicious tuning of the leaving group on the N–O electrophile such that it possess well-matched reactivity for the corresponding alkyl nickelacycle intermediate. Congrats to Taeo, José, and Zi-Qi, and thanks to our collaborators from BMS, Klement and Peter, for a great collaboration.
For a link to the pre-print, click here: https://chemrxiv.org/engage/chemrxiv/article-details/61b14f9a7ada95b46a6e62ee
We’ve recently started exploring foreign parts of the periodic table, and turned our attention to sulfur. Organosulfur compounds are useful in various settings, and three-component couplings represent a fast, efficient, and modular way to synthesize such compounds. Classical carbosulfenylation (the addition of a carbon and a sulfur(II) group across an alkene) proceed via a reactive thiiranium intermediate that is then opened in an SN2 fashion, with limitations arising from the electrophilic nature of the sulfenyl transfer groups typically employed. We envisioned an alternative organometallic approach relying on three-component catalytic coupling of organoboron nucleophiles, sulfenyl electrophiles, and unactivated alkenes. This novel transformation was enabled by the discovery of a new family of N–S electrophiles that possess perfectly balanced reactivity, which could be understood through computational studies. Hats off to the team, graduate student co-authors Zi-Qi and Taeho, and former SURF intern Yilin, who has since returned to UCSB to finish her senior year of college.
For a link to the pre-print, click here: https://chemrxiv.org/engage/chemrxiv/article-details/61a7d3e0f35d4ca9794de71d
In a new book chapter that appears online this week, Luke, Alena, Taeho, and Zi-Qi review the broad field of metal-mediated difunctionalization of unsaturated organic compounds (i.e., those containing a carbon–carbon π-bond). The chapter is part of the forthcoming book Comprehensive Organometallic Chemistry IV edited by Prof. Ian Tonks.
Click here for a link to the article: https://www.sciencedirect.com/science/article/pii/B9780128202067000962
This week Keary was selected together with Prof. Thomas Bennett (Cambridge) to receive the 2021 ChemComm Emerging Investigator Lectureship. The award recognizes scientists in the early stages of their independent academic careers who have made exceptional contributions to the field of chemistry. As part of the award, in 2022 Keary will give a series of lectures in both in-person and virtual format . Congrats to Keary and the entire Engle lab past and present for contributing the science being recognized!
For more information, click here: https://blogs.rsc.org/cc/2020/11/16/chemcomm-emerging-investigator-lectureship-2021-nominations-now-open/