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Metal‐Free Tandem Rearrangement/Lactonization: Access to 3,3‐Disubstituted Benzofuran‐2‐(3H)‐ones
Authors:Micol Santi  Darren M C Ould  Jan Wenz  Yashar Soltani  Rebecca L Melen  Thomas Wirth
Abstract:A novel metal‐free synthesis of 3,3‐disubstituted benzofuran‐2‐(3H)‐ones through reacting α‐aryl‐α‐diazoacetates with triarylboranes is presented. Initially, triarylboranes were successfully investigated in α‐arylations of α‐diazoacetates, however in the presence of a heteroatom in the ortho position, the boron enolate intermediate undergoes an intramolecular rearrangement to form a quaternary center. The intermediate cyclizes to afford valuable 3,3‐disubstituted benzofuranones in good yields.
Keywords:benzofuranone  boron  diazo compounds  metal-free conditions  rearrangement
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