Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on
Junya Kitano1, Yuji Nishii1, Masahiro Miura2
1Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka565-0871, Japan.
Abstract:
Benzofuran is a privileged structure in many bioactive compounds; however, the controlled synthesis of C2,C3-nonsubstituted benzofurans has been scarce. In particular, cumbersome multistep processes are inevitable for the most inaccessible C4-substituted isomers. Herein, we report a Rh-catalyzed direct vinylene annulation of readily available m-salicylic acid derivatives with vinylene carbonate to achieve selective construction of C4-substituted benzofurans. The Weinreb amide directing group facilitated the following product derivatization. The reaction mechanism was investigated by DFT calculations.
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