Journal
ORGANIC LETTERS
Volume 23, Issue 19, Pages 7597-7602Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02813
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Funding
- National Natural Science Foundation of China [21772136, 21772135]
- Sichuan Science and Technology Program [19YYJC2834]
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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.
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.
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