Redox-Neutral Ru(0)-Catalyzed Alkenylation of 2-Carboxaldimine-heterocyclopentadienes.

J Org Chem

Sorbonne Université, Faculté des Sciences et Ingénierie, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, 4 Place Jussieu, 75005 Paris, France.

Published: April 2022

A new Ru(CO)-catalyzed directed alkenylation of 2-carboxaldimine-heterocyclopentadienes has been accomplished. This process allows coupling of furan, pyrrole, indole, and thiophene 2-carboxaldimines with electron-poor alkenes such as acrylates, vinylsulfones, and styrenes. This regio- and chemoselective oxidative C-H coupling does not require the presence of an additional sacrificial oxidant. Density functional theory calculations allowed us to propose a mechanism and unveiled the nature of the H acceptor.

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http://dx.doi.org/10.1021/acs.joc.1c03044DOI Listing

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