期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 10, 页码 6769-6780出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00470
关键词
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资金
- JSPS KAKENHI [18H04264, 18H04233, JP21K05016]
- International Institute for Carbon-Neutral Energy Research (WPI-I2CNER) from MEXT, Japan
- Research Centre for Computation Science, the National Institutes of Natural Sciences, Japan [21-IMS-C046, 22-IMS-C46]
- Grants-in-Aid for Scientific Research [18H04264, 18H04233] Funding Source: KAKEN
C-H functionalization is a powerful tool for modifying bioactive compounds and creating new active molecules in late-stage transformations. However, its application is limited. This study demonstrates the efficient catalysis of an iridium-salen complex in asymmetric carbene C-H insertion reactions, achieving high stereoselectivity and regioselectivity.
C-H functionalization has recently received con-siderable attention because C-H functionalization during the late-stage transformation is a strong and useful tool for the modificationof the bioactive compounds and the creation of new activemolecules. Although a carbene transfer reaction can directlyconvert a C-H bond to the desired C-C bond in a stereoselectivemanner, its application in late-stage material transformation islimited. Here, we observed that the iridium-salen complex6exhibited efficient catalysis in asymmetric carbene C-H insertionreactions. Under optimized conditions, benzylic, allylic, andpropargylic C-H bonds were converted to desired C-C bondsin an excellent stereoselective manner. Excellent regioselectivitywas demonstrated in the reaction using not only simple substrate but also natural products, bearing multiple reaction sites.Moreover, based on the mechanistic studies, the iridium-catalyzed unique C-H insertion reaction involved rate-determiningasynchronous concerted processes
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