Abstract
In the presence of catalytic amounts of RhH(PPh3)4, 1,2-bis(diphenylphosphino)ethane (dppe), and dimethyl disulfide, ketones without α-activating groups were α-methylthiolated with 1,2-diphenyl-2-methylthio-1-ethanone giving α-methylthio ketones. The reaction of unsymmetrical ketones proceeded at the more substituted carbons. The initial formation of kinetic α-methylthiolated products followed by their rearrangement to thermodynamic products was observed in the reaction of α-phenyl ketones. Aldehydes, phenylacetate, and phenylacetonitrile were also α-methylthiolated under these conditions.
Original language | English |
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Pages (from-to) | 2305-2312 |
Number of pages | 8 |
Journal | Tetrahedron |
Volume | 67 |
Issue number | 12 |
DOIs | |
Publication status | Published - 2011 Mar 25 |
Keywords
- C-H activation
- Equilibrium
- Ketone
- Methylthiolation
- Rhodium catalyst
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry