Practical 1,2-Diarylation of Alkenes Directed by Simple Amides – Now In Press

The nickel team strikes again, with a final version of our nickel-catalyzed alkene 1,2-diarylation paper appearing online in final form at J. Am. Chem. Soc. (click here). Through identification of an effective electron-deficient olefin ligand, this catalytic system allow for use of simple commonly encountered primary, secondary, and tertiary amides as directing groups, including those that are native to various target compounds of interest. Additionally, this work represents one of the rare cases in 1,2-diarylation chemistry where an aryl boronic acid derivative can be used as the nucleophilic coupling partner. Congratulations to Joe, Roman, Van, and Malkanthi from the Engle lab and Steve and Martin from Bristol-Myers Squibb. Thanks to everyone involved for a great collaboration. In case anyone missed it, a pre-print of this work was published on ChemRxiv back in early November (click here).

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Three-Component Umpolung Carboamination – Now in Press

Vincent and Joe’s paper on three-component, nickel-catalyzed umpolung carboamination of alkenyl carbonyl compounds appears online today in final form at ACS Catalysis (click here). This unique transformation enables syn-selective delivery of nitrogen and carbon substituents of choice across an alkene and allows for formation of exceptionally hindered C(sp3)–C and C(sp3)–N bonds. It represents one of the few rare examples in which amine-directed N–O electrophiles (first used in two-component cross-couplings by Johnson) have been integrated into a nickel-mediated alkene functionalization process. It’s a special treat to highlight that the project lead, Vincent (now a grad student upstairs with Ryan Shenvi), performed this work as his senior-year undergrad research project while at UCSD. Props to Joe for great mentorship, and congrats to both authors! In case anyone missed it, a pre-print of this work was published on ChemRxiv back in early November (click here).

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New High School Intern Joins the Lab

Our newest high school intern Matt joins us from San Diego High School and will be working with A.M.R (G3). Matt has found his new favorite piece of glassware, the rotavap cow, and can rotavap down 4 reactions at once. Welcome Matt!