期刊
ORGANIC CHEMISTRY FRONTIERS
卷 9, 期 19, 页码 5272-5280出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00943a
关键词
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资金
- National Natural Science Foundation of China [22072035]
- Zhejiang Provincial Natural Science Foundation of China [LY20B030006, LY21B030007, LR22B020002, LY22B020006]
We report a highly selective silane synthesis method, which enables the formation of silicon-carbon bonds by capturing silyl metal intermediates generated from silicon reagents through palladium or copper catalysis. This method allows for the efficient synthesis of asymmetric difluorocyclopropanes and achieves high enantioselectivity with appropriate ligands.
We report herein that a highly regioselective silicon-carbon bond-forming silylation of unsymmetric gem-difluorocyclopropenes based on Si-C or Si-B bond cleavage of organosilicon reagents was achieved using palladium or copper catalysis through the capture of in situ formed silyl metal intermediates. These reactions effectively deliver structurally diverse difluorocyclopropanes, including sila-difluorobicyclo[4.1.0]heptanes and silyl gem-difluorocyclopropanes, in a stereoselective manner, in which two types of silicon-containing gem-difluorocyclopropanes can be achieved in good yields with high regioselectivity, and silyl gem-difluorocyclopropanes can be obtained with excellent enantioselectivity (up to 97% ee) in the presence of a chiral TADDOL-derived phosphoramidite ligand.
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