Deuterium-Labeling Studies on the C–H/Olefin Coupling of Aromatic Ketones Catalyzed by Fe(PMe₃)₄

Abstract

Deuterium-labeling experiments were performed for the Fe(PMe₃)₄-catalyzed C–H/olefin coupling using a deuterium-labeled aromatic ketone with various alkenes. While the reactions with a variety of alkenes provided the linear alkylation products formed via 1,2-insertion of alkene into an Fe–H bond, the reversible 2,1-insertion proceeded during the reaction highly depends on the choice of the alkene. No H/D scrambling resulting from 2,1-insertion/β-elimination was detected for the reactions with a vinylsilane and N-vinylcarbazole, but the reactions­ with styrenes are considered to involve rapid 2,1-insertion/ β-elimination processes to cause significant levels of H/D scrambling.

Key words

C–H/olefin coupling - iron catalyst - deuterium-labeling experiments - mechanism - styrene

Publication History

Received: 30 March 2021

Accepted after revision: 27 April 2021

Article published online:
19 May 2021

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