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Regioselective Metal-Free Aza-Heck Reactions of Terminal Alkenes Catalyzed by Phosphine Selenides.

A new interesting article has been published in Org Lett. 2018 Oct 19. doi: 10.1021/acs.orglett.8b03159. [Epub ahead of print] and titled:

Regioselective Metal-Free Aza-Heck Reactions of Terminal Alkenes Catalyzed by Phosphine Selenides.

Authors of this article are:

Zheng T, Tabor JR, Stein ZL, Michael FE.

A summary of the article is shown below:

Phosphine selenides are introduced as an alternate class of selenium-based catalysts for the aza-Heck reaction of alkenes. Using these catalysts, a range of terminal alkenes react with NFBS to give oxidative amination products. Judicious choice of phosphine ligand gives greater regio- and stereoselectivity than with diphenyl diselenide, enabling the selective formation of E terminal enimides in high yields. Isotope-labeling experiments and measurements of kinetic isotope effects reveal that the reaction occurs stereospecifically via irreversible anti addition, followed by rate-determining syn elimination.

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