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Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones
Micol Santi1, Darren M C Ould1, Jan Wenz1
1School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, Wales, UK.
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.
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