Iron-Catalyzed Heck-Type Alkenylation of Functionalized Alkyl Bromides

Kailong Zhu, Joanne Dunne, Michael Patrick Shaver, Stephen P Thomas

Research output: Contribution to journalArticlepeer-review

Abstract

The ability of iron to controllably generate alkyl radicals from alkyl halides as a key step in atom transfer radical polymerization (ATRP) has been adapted to facilitate a formal Heck cross-coupling between styrenes and functionalized alkyl bromides. A simple FeCl2 catalyst in a coordinating solvent gave excellent activity without the need for expensive ligands. Tertiary, secondary and even primary alkyl bromides are tolerated to give the products in moderate to good yields (up to 93% yield). The easily accessible reagents and operational simplicity make this reaction a method of choice for the alkenylation of alkyl halides, especially for functionalized tertiary alkyl halides which are difficult to target by classic palladium-catalyzed Heck reactions because of the competing β-hydride elimination.
Original languageEnglish
JournalACS Catalysis
DOIs
Publication statusPublished - 22 Feb 2017

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