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Updated: Aug 25, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Coupling-isomerization-coupling sequences switched on by propargyl alcohol-enone-isomerization
Roland U Braun1, Thomas J J Müller
1Organisch-Chemisches Institut der Ruprecht-Karls- Universität Heidelberg, Im Neuenheimer Feld 270, Heidelberg, Germany.
Abstract:
The coupling-isomerization-reaction (CIR) of an electron-deficient halide 1 with 1-(p-bromo phenyl) propyne-1-ol (2) leads to an in-situ activation of the carbon-bromine bond towards oxidative addition and has been elaborated to a consecutive CIR-coupling sequence where subsequent palladium catalyzed coupling reactions such as Sonogashira, CIR, Heck, or Suzuki reactions allow a rapid construction of more complex frameworks in a one-pot reaction and in moderate to good yields.
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