期刊
GREEN CHEMISTRY
卷 19, 期 22, 页码 5361-5366出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7gc02690k
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资金
- Narodowe Centrum Nauki [2014/15/D/ST5/02731]
- Rutgers University
Iron-catalyzed cross-coupling has emerged as a powerful tool for sustainable catalysis. However, by far the most common ligand in iron-catalyzed cross-couplings for preparative and industrial applications is reprotoxic NMP. Herein, we report that cyclic ureas (DMI, DMPU) are efficient and sustainable alternatives to NMP in iron-catalyzed alkylations of aryl chlorides and tosylates with alkyl Grignard reagents. This environmentally benign method accomplishes traditionally challenging C(sp(2))-C(sp(3)) cross-coupling with organometallics possessing beta-hydrogens with efficiency matching or superseding NMP. The reaction is compatible with a variety of electrophilic functional handles. Applications to double and site-specific alkylations are described. The potential of this method is highlighted in the key coupling in the synthesis of a dual NK1/serotonin receptor antagonist. Considering the pivotal importance of sustainable iron-catalysis, we believe that the method will find wide application in green chemistry.
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