Journal
SYNTHESIS-STUTTGART
Volume 53, Issue 18, Pages 3383-3389Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1706040
Keywords
C-H/olefin coupling; iron catalyst; deuterium-labeling experiments; mechanism; styrene
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Funding
- JST CREST [JPMJCR20R1]
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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.
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.
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