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.


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.