Skeleton Reorganization of Substituted Benzocyclobutenols through Rh-Catalyzed C-C Bond Cleavage Manipulated by Hydrogen Transfer

Although transition-metal-catalyzed C-C bond activation has been investigated extensively, C-C bond cleavage manipulated by hydrogen transfer has been unexplored. In this work, we disclose a skeleton reorganization of alkene-tethered benzocyclobutenols through Rh-catalyzed C-C bond cleavage coupled with intra- and intermolecular hydrogen transfer. The reaction pathway was well-tuned by the catalytic systems. As a result, divergent benzofurans bearing 4-beta-hydroxy or 4-beta-keto moieties were synthesized under pH- and redox-neutral conditions.

Automated summary

This study unveiled a skeleton reorganization of alkene-tethered benzocyclobutenols through Rh-catalyzed C-C bond cleavage coupled with intra- and intermolecular hydrogen transfer, leading to the synthesis of divergent benzofurans bearing 4-beta-hydroxy or 4-beta-keto moieties under pH- and redox-neutral conditions. The reaction pathway was finely tuned by the catalytic systems.