Abstract
C(sp2)–Sn bonds generally react more quickly than C(sp3)–Sn bonds in tin–boron exchange processes, and discrimination between (hetero)aryl groups to be transferred from tin to boron and those to remain at the tin atom (usually methyl groups) is reliable. Conversely, transmetalation of benzylic carbon–tin bonds is disfavored, and the chemoselectivity against other C(sp3)–Sn bonds at the tin atom is poor. That inherent problem is overcome by the installation of one or more Me3SiCH2 (TMSM) groups at the tin atom as nontransferable substituents. With these groups, the tin–boron metathesis of benzylic C(sp3)–Sn bonds occurs cleanly and rapidly. The efficiency of the new method is demonstrated in the demanding synthesis of C6F5-substituted dihydroborepines with binaphthyl backbones.
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