Abstract
Para-Methoxybenzyl methyl ether acts as an alkylating agent for thiols in the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine base in good yields (58-96%). Aryl ketones are alkylated under similar conditions, probably through an enol silane intermediate, also in high yields (67-95%). The active alkylating species is likely a p-methoxybenzyl cation.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5213-5215 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 55 |
| Issue number | 37 |
| DOIs | |
| State | Published - Jul 2005 |
Funding
We thank the National Science Foundation RUI program ( CHE-1057591 ), the Thomas F. Jeffress and Kate Miller Jeffress Memorial Trust ( J-1006 ), and Research Corporation ( CC6975/7096 ) for funding. D.C.O. and D.N.C. gratefully acknowledge the University of Richmond College of Arts and Sciences for summer fellowships. E.H. gratefully acknowledges the Howard Hughes Medical Institute for a summer fellowship. J.T.R. gratefully acknowledges the Grainger Science Initiative and the American Chemical Society Petroleum Research Fund for summer fellowships (there were two fellowships, one funded by Grainger and one by ACS-PRF). We thank the Donors of the American Chemical Society Petroleum Research Fund for partial support of this research. We are indebted to the National Science Foundation (CHE-0541848), and the University of California-Riverside for mass spectral data.
Keywords
- Alkylation
- Enol silanes
- Methyl ethers
- Silyl triflates
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry