Abstract
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 β-substituted styrene derivatives. Mechanistic experiments using deuterium-labeled indole substrate and Grignard reagent provided insight into the cobalt-mediated C -H activation step, which likely involves exchange of the C2-hydrogen atom of the former and the β-hydrogen atoms of the latter. ...? but thats secondary: A catalytic system consisting of CoBr2, N-heterocyclic carbene, and cyclohexylmagnesium bromide promotes the imine-directed addition of indoles to nonconjugated aryl-substituted alkenes through tandem alkene isomerization-hydroarylation, affording 1,1-diarylalkane derivatives with exclusive regioselectivity. Deuterium-labeling experiments revealed the involvement of the secondary alkyl Grignard reagent in the cobalt-mediated C -H activation process.
Original language | English |
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Pages (from-to) | 1242-1246 |
Number of pages | 5 |
Journal | Chemistry - An Asian Journal |
Volume | 9 |
Issue number | 5 |
DOIs | |
Publication status | Published - 2014 May |
Externally published | Yes |
Keywords
- alkenes
- alkylation
- C -H functionalization
- cobalt
- indoles
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry