Systematic Studies of Functional Group Tolerance and Chemoselectivity in Carbene-Mediated Intramolecular
Haruki Kanda1, Ayaka Okabe1, Shingo Harada1
1Graduate School of Pharmaceutical Sciences, Chiba University.
Abstract:
Generating reliable data on functional group compatibility and chemoselectivity is essential for evaluating the practicality of chemical reactions and predicting retrosynthetic routes. In this context, we performed systematic studies using a functional group evaluation kit including 26 kinds of additives to assess the functional group tolerance of carbene-mediated reactions. Our findings revealed that some intermolecular heteroatom-hydrogen insertion reactions proceed faster than intramolecular cyclopropanation reactions. Lewis basic functionalities inhibited rhodium-catalyzed C-H functionalization of indoles. While performing these studies, we observed an unexpected C-H functionalization of a 1-naphthol variant used as an additive.
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