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Synthesis of 1,1-silylboranes and silylboronates

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Enantioenriched 1,1-silylboryl alkanes are highly valued building blocks in asymmetric synthesis as well as medicinal chemistry. An enantioselective cobalt-catalyzed hydrosilylation/hydroboration cascade of terminal alkynes offers chemo-, regio-, and stereoselectivity exquisitely controlled by a single set of metal catalyst and ligand.
S. Jin, K. Liu, S. Wang, Q. Song, J. Am. Chem. Soc., 2021, 143, 13124-13134.


Enantioenriched 1,1-silylboryl alkanes are highly valued building blocks in asymmetric synthesis as well as medicinal chemistry. An enantioselective cobalt-catalyzed hydrosilylation/hydroboration cascade of terminal alkynes offers chemo-, regio-, and stereoselectivity exquisitely controlled by a single set of metal catalyst and ligand.
S. Jin, K. Liu, S. Wang, Q. Song, J. Am. Chem. Soc., 2021, 143, 13124-13134.


A base-mediated borylsilylation of benzylic ammonium salts provides geminal silylboronates bearing benzylic proton under mild reaction conditions. Deaminative silylation of aryl ammonium salts was also achieved in the presence of LiOtBu. Both methods offer high efficiency, mild reaction conditions, and good functional group tolerance for late-stage functionalization of amines.
W.-Y. Qi, J.-S. Zhen, X.-h. Xu, X. Du, Y.-h. Li, H. Yuan, Y.-S. Guan, X. Wei, Z.-Y. Wang, G. Liang, Y. Luo, Org. Lett., 2021, 23, 5988-5992.