Journal
ORGANIC LETTERS
Volume 18, Issue 9, Pages 2086-2089Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00712
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Funding
- Stichting Fundatie van de Vrijvrouwe van Renswoude
- Stichting Nijmeegs Universiteits Fonds (SNUF)
- GlaxoSmithKline
- EPSRC
- Engineering and Physical Sciences Research Council [EP/K00803X/1, 1512270] Funding Source: researchfish
- EPSRC [EP/K00803X/1] Funding Source: UKRI
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A one-pot process for the synthesis of unsymmetrical sulfoxides using organometallic nucleophiles is described. Sulfur dioxide, delivered from the surrogate DABSO (DABCO-bis(sulfur dioxide)), acts as the initial electrophile and combines with the first organometallic reagent to generate a sulfinate intermediate. In situ conversion of the sulfinate to a sulfinate silyl ester, using TMS-Cl (trimethylsilyl chloride), generates a second electrophile, allowing addition of a second organometallic reagent. Organolithium or Grignard reagents can be employed, delivering sulfoxides in good to excellent yields.
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