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

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/beta-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/ beta-elimination processes to cause significant levels of H/D scrambling.

Automated summary

Deuterium-labeling experiments were conducted for Fe(PMe3)(4)-catalyzed C-H/olefin coupling using a deuterium-labeled aromatic ketone and various alkenes. The choice of alkene significantly affects the reversible 2,1-insertion process during the reaction. While no H/D scrambling was detected for reactions with vinylsilane and N-vinylcarbazole, significant levels of H/D scrambling were observed for reactions with styrenes, suggesting rapid 2,1-insertion/beta-elimination processes.