Abstract
Comprehensive SummaryIt is very important to develop efficient synthetic strategies for site‐specific functionalization of tetrahydroquinolines due to their indispensable roles in pharmaceutical and agrochemical industries. We apply hard/soft acid/base (HSAB) theory to selective reduction of quinoline and achieve a series of C3‐functionalized tetrahydroquinoline in high to excellent yields (up to 99%) under mild conditions with the catalysis of B(C6F5)3. A series of in situ NMR reactions are also performed to investigate this cascade reaction. Moreover, AB type monomer 6‐(dimethylsilyl) quinoline and AA/BB type monomer 6,6'‐biquinoline are synthesized for polymer synthesis, which represents the first example of silicon bridged polytetrahydroquinoline.
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