Gamma-Selective Alkene Hydroarylation with Arylboronic Acids

As part of an ongoing collaboration with Pfizer, today we report a new method for achieving γ-selective hydroarylation of alkenyl carbonyl compounds, which is available as a pre-print on ChemRxiv (click here).  This reaction is notable for its simplicity, practicality, and functional group tolerance. Because of the ubiquity of arylboronic acids in pharma and in academia, this protocol offers a powerful approach to appending an aryl group of one’s choosing to the γ-position of a carboxylic acid substrate. Congrats to all of the authors: Rei, Tanner, Kin, and Rohan from TSRI; and Gary, Shouliang, Mingying, Fen, and Indra from Pfizer. It was great working with the Pfizer team to field-test the method and to identify valuable heterarylboronic acids that would be of interest to medicinal chemists. Special shoutout to high school student co-author, Rohan, who worked with us earlier this year as part of his junior year internship. Great work, team! Stay tuned for the peer-reviewed version.

Hydroarylation

Catalytic 1,3-Diene Synthesis via C(alkenyl)–H Activation

In an Article appearing online today in J. Am. Chem. Soc., the Engle lab and Liu lab (U Pittsburgh) report a detailed study of palladium(II)-catalyzed C(alkenyl)–H activation, including optimization of a method to prepare structurally diverse 1,3-dienes, organometallic synthesis of key intermediates relevant to catalysis, and experimental/computational studies to interrogate the reaction mechanism. Congrats to the whole team: Mingyu, Pusu, and Malkanthi from Scripps; and Yanyan from Pitt. Special shout out to undergraduate co-author Pusu, who was a visiting student from Nankai university for six months. Thanks to the Liu lab for another fruitful collaboration! Way to go, everyone! Click here for a link to the paper.

diene

Keary Receives 2018 Bayer Early Excellence in Science Award

Congratulations to Keary, who was selected as a recipient of the prestigious 2018 Bayer Early Excellence in Science Award. The prize is awarded by an independent scientific committee of Bayer Science & Education Foundation and will be presented on June, 25 at the Bayer Foundation Day in Berlin. Congratulations to Keary and the entire Engle lab!

For a link to the Bayer press release, click here.
For a link to the TSRI News & Views highlight, click here.

Catalytic, enantioselective method for allenyl boronate synthesis accepted for publication

Our manuscript describing a method to achieve catalytic, enantioselective 1,4-hydroboration of 1,3-enynes was accepted for publication in ACS Catal. Congratulations to the authors, De-Wei, Yiyang (Elaine), Mingyu, Zhen, Malkanthi, Jason, and Keary. We would also like to acknowledge our collaborators at Boehringer-Ingelheim, Dan Fandrick, Jeff Song, and Chris Senanayake, for valuable discussion and guidance. BI has a longstanding interest in allenyl boronates and related organoboron nucleophiles. (For representative papers, see: J. Am. Chem. Soc. 20101327600Org. Lett.20101288Org. Lett. 201113, 5616). Their interest in and experience with this family of compounds played an important role in the genesis of this project, and the Engle lab is looking forward to many stimulating interactions with the BI team moving forward. Click here for a link to the paper. A pre-print of this work was previously published on ChemRxiv (click here).

allenyl

IMG_0195(not pictured: Yiyang (Elaine) and Mingyu)

judging at the orange county science fair

Andrew, Tanner and David headed up to OC for the day to help judge the high school and junior high county science fair. We awarded the “Engle Lab Prize” to an individual who did not get the result they wanted but showed persistence and dedication to their research. In the senior division we awarded the prize for the work done on monitoring sugar conversion in bananas by varying ethylene levels, and in the Junior division for the poster on measuring “sugar” concentration of different types of sugar by quantifying the amount of CO2 produced during fermentation. Congratulations to the winners of the Engle Lab Prize and all the other participants for their great work!