Systematic Studies of Functional Group Tolerance and Chemoselectivity in Carbene-Mediated Intramolecular Cyclopropanation and Intermolecular C-H Functionalization

Chem Pharm Bull (Tokyo). 2024;72(3):313-318. doi: 10.1248/cpb.c24-00022.ABSTRACTGenerating 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.PMID:38494725 | DOI:10.1248/cpb.c24-00022
Source: Chemical and Pharmaceutical Bulletin - Category: Drugs & Pharmacology Authors: Source Type: research