Thionyl Tetrafluoride Click Chemistry

  • ChemPubSoc Europe Logo
  • Author: Angewandte Chemie International Edition
  • Published Date: 13 February 2018
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Thionyl Tetrafluoride Click Chemistry

Many sulfur(VI) fluoride compounds contain S–F bonds that are thermodynamically stable and redox-silent. However, S–F exchange occurs easily with specific nucleophiles.


Barry Sharpless, The Scripps Research Institute, La Jolla, CA, USA, and colleagues have developed a click reaction named SuFEx (Sulfur Fluoride Exchange) that sequentially replaces the four S–F bonds of thionyl tetrafluoride (SOF4) to efficiently form diverse sulfur compounds. A primary amine (R1–NH2) is reacted with SOF4 to produce tetrahedral iminosulfur oxydifluorides (R1–N=SOF2, pictured). The remaining two fluoride groups can be exchanged sequentially with a range of nucleophiles, such as amine and aryloxy nucleophiles, to form the desired products.


The researchers created S–C bonds from these functionalized S(VI) species by selectively substituting one of the two remaining F atoms with an aryllithium reagent. The resulting sulfonimidoyl fluorides undergo a further nucleophilic substitution to produce a diverse array of useful functional groups, including sulfoximines, sulfonimidamides, and sulfonimidates.


 

Article Views: 792

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH