Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 9, Issue 5, Pages 1242-1246Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201400135
Keywords
alkenes; alkylation; CH functionalization; cobalt; indoles
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Funding
- Singapore National Research Foundation , [NRF-RF2009-05]
- Nanyang Technological University
- JST, CREST
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A cobalt-N-heterocyclic carbene catalyst generated from CoBr2, imidazolium salt, and cyclohexylmagnesium bromide was found to promote the imine-directed C2-alkylation of indoles with nonconjugated arylalkenes through a tandem alkene isomerization-hydroarylation process, affording 1,1-diarylalkanes with exclusive regioselectivity. The feasibility of the tandem catalysis was demonstrated for allyl-, homoallyl-, and bishomoallylbenzene derivatives. The catalytic system is also applicable to a variety of -substituted styrene derivatives. Mechanistic experiments using deuterium-labeled indole substrate and Grignard reagent provided insight into the cobalt-mediated CH activation step, which likely involves exchange of the C2-hydrogen atom of the former and the -hydrogen atoms of the latter.
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