Enantioselective three-component 1,2-diarylation and -arylalkenylation of alkenes – Pre-print now online

After >3 years of work, we are happy to share a ChemRxiv pre-print today describing a solution to a longstanding problem, stereoinduction in intermolecular arylnickel migratory insertion into alkenes, which we investigated in the context of interest in catalytic 1,2-dicarbofunctionalization. We found that a sterically bulky, achiral sulfonamide directing group works in synergy with a specially tuned hemilabile ligand (Bn-biOX) to promote high enantioselectivity with a variety of arylboron and aryl iodide coupling partners. Through use of experimental and computational techniques, we elucidated the mechanism of this three-component catalytic coupling, which involves an enantiodetermining migratory insertion step, which is distinct from previous radical-based methods. It was a great collaborative effort between our lab (Omar, Taeho, Pranali, Camille, and Joe), the Liu lab at the University of Pittsburgh (Turki), the Scripps Automated Synthesis Facility (Brittany, Quynh, Emily, and Jason), and Bristol Myers Squibb (Steve). Congrats to everyone!

For a link to the pre-print in ChemRxiv, click here: https://chemrxiv.org/engage/chemrxiv/article-details/62b40edc0bbbc1d407726e34