0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via Variation 2: Ylide Generation by Desilylation of a Sulfonium Salt

DOI: 10.1055/sos-SD-037-00188

Aggarwal, V. K.; Crimmin, M.; Riches, S.Science of Synthesis, (200837347.

An alternative method for the generation of sulfonium methylides is by the fluoride ion induced desilylation of a suitably functionalized sulfonium salt {see also Science of Synthesis, Vol. 27 [Heteroatom Analogues of Aldehydes and Ketones (Section]}.[‌141‌] Diphenyl[(trimethylsilyl)methyl]sulfonium trifluoromethanesulfonate (47) may be desilylated by treatment with an excess of cesium fluoride in a polar aprotic solvent at room temperature to generate diphenylsulfonium methylide (Scheme 44).[‌142‌] One major advantage of this variation is that it allows the regioselective generation of ylides that are contra-thermodynamic to those expected by deprotonation.[‌143‌] Diphenyl[(trimethylsilyl)methyl]sulfonium trifluoromethanesulfonate (47) may, in turn, be synthesized by the alkylation of diphenyl sulfide with (trimethylsilyl)methyl trifluoromethanesulfonate.

Meeeee 88 Meeeeeeee Meeeeeeee Meeeeeeeee ee Meeeeeee Mee Meeeeee Meeeeeeeeeee[‌888‌]