Formic Acid Mediated Direct Z-Selective Reductive Coupling of Dienes and Aldehydes

06 May 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We demonstrate that formic acid mediates the Rh-catalyzed, Z-selective coupling of dienes and aldehydes. The process is distinguished by broad tolerance towards reducible or electrophilic groups. Kinetic analysis suggests that generation of the catalytically active Rh-intermediate by ligand dissociation is the rate determining step. The rapid generation and trapping of Rh-allyl intermediates is key to preventing chain-walking isomerization events that plague related protocols. Insights gained through this study may have wider implications in selective metal-catalyzed hydrofunctionalization reactions.

Keywords

reductive coupling
chemoselectivity
Z-olefins
rhodium

Supplementary materials

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Red Coupling SI MAY04 FULL
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