Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles Article Swipe

View

Related Concepts

Chemistry Imine Transmetalation Regioselectivity Reagent Aryl Reductive elimination Migratory insertion Oxidative addition Combinatorial chemistry Heck reaction Catalysis Hydride Organic chemistry Medicinal chemistry Palladium Alkyl Hydrogen

Bijay Shrestha , Prakash Basnet , Roshan K. Dhungana , Shekhar KC , Surendra Thapa , Jeremiah M. Sears , Ramesh Giri ·

YOU? · · 2017 · Open Access · · DOI: https://doi.org/10.1021/jacs.7b06340 · OA: W2738844118

We disclose a strategy for Ni-catalyzed dicarbofunctionalization of olefins in styrenes by intercepting Heck C(sp<sup>3</sup>)-NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometalation and stabilizing the Heck C(sp<sup>3</sup>)-NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely substituted 1,1,2-triarylethyl products that occur as structural motifs in various natural products.