4.8 Article

Palladium-Catalyzed Disilylation and Digermanylation of Alkene Tethered Aryl Halides: Direct Access to Versatile Silylated and Germanylated Heterocycles

Journal

ORGANIC LETTERS
Volume 22, Issue 9, Pages 3679-3683

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01169

Keywords

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Funding

  1. University of Toronto
  2. Natural Science and Engineering Research Council (NSERC)
  3. Alphora Research Inc.
  4. Kennarshore Inc.
  5. Deutsche Forschungsgemeinschaft [IRTG 2027]
  6. NSERC
  7. Province of Ontario (QEII)
  8. Walter C. Sumner Memorial Fellowship

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A method for the palladium-catalyzed disilylation and digermanylation of aryl halides bearing a tethered alkene has been developed. The mechanism is thought to proceed via Heck-type cyclization, followed by C-H activation, resulting in a reactive fused-palladacycle. A wide variety of disilylated and digermanylated heterocycles are obtained from readily available aryl halides in high yields with various functional groups. Moreover, the developed protocol proved to be highly diastereoselective.

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