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One-Pot Sulfoxide Synthesis Exploiting a Sulfinyl-Dication Equivalent Generated from a DABSO/Trimethylsilyl Chloride Sequence

Danny C. Lenstra, Vincent Vedovato, Emmanuel Ferrer Flegeau, Jonathan Maydom and Michael C. Willis*

*Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom, Email: michael.willischem.ox.ac.uk

D. C. Lenstra, V. Vedovato, E. F. Flegeau, J. Maydom, M. C. Willis, Org. Lett., 2016, 18, 2086-2089.

DOI: 10.1021/acs.orglett.6b00712 (free Supporting Information)


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Abstract

Sulfur dioxide, delivered from the surrogate DABSO, combines as electrophile with an organometallic reagent to generate a sulfinate intermediate. In situ conversion of the sulfinate to a sulfinate silyl ester, using TMS-Cl, generates another electrophile, allowing addition of a second organometallic reagent. Both organolithium or Grignard reagents deliver sulfoxides in very good yields.

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DABSO-Based, Three-Component, One-Pot Sulfone Synthesis

A. S. Deeming, C. J. Russell, A. J. Henessy, M. C. Willis, Org. Lett., 2014, 16, 150-153.


Key Words

sulfoxides


ID: J54-Y2016