无金属串联重排/内酯化反应：合成3,3-二取代苯并呋喃-2-(3H)-酮
Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones.
作者信息
Santi Micol, Ould Darren M C, Wenz Jan, Soltani Yashar, Melen Rebecca L, Wirth Thomas
机构信息
School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, Wales, UK.
出版信息
Angew Chem Int Ed Engl. 2019 Jun 3;58(23):7861-7865. doi: 10.1002/anie.201902985. Epub 2019 Apr 10.
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.
本文报道了一种通过α-芳基-α-重氮乙酸酯与三芳基硼烷反应，无金属合成3,3-二取代苯并呋喃-2-(3H)-酮的新方法。最初，三芳基硼烷已成功应用于α-重氮乙酸酯的α-芳基化反应，但在邻位存在杂原子的情况下，硼烯醇盐中间体发生分子内重排形成季碳中心。该中间体环化，以良好的产率得到有价值的3,3-二取代苯并呋喃酮。
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