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

A new Ru3(CO)12-catalyzed directed alkenylation of2-carboxaldimine-heterocyclopentadienes has been accomplished.This process allows coupling of furan, pyrrole, indole, andthiophene 2-carboxaldimines with electron-poor alkenes such asacrylates, vinylsulfones, and styrenes. This regio- and chemo-selective oxidative C-H coupling does not require the presence ofan additional sacrificial oxidant. Density functional theory calculations allowed us to propose a mechanism and unveiled the nature ofthe H2acceptor.

Automated summary

A method for the directed alkenylation of 2-carboxaldimine-heterocyclopentadienes using Ru3(CO)12 catalyst has been developed. This reaction enables coupling of various electron-poor alkenes with furan, pyrrole, indole, and thiophene 2-carboxaldimines, and does not require additional sacrificial oxidants. Mechanistic insights have been obtained through density functional theory calculations.